Diterpenes of Flowering Plants

Diterpenes of Flowering Plants
F. Seaman F. Bohlmann
C. Zdero T.J. Mabry
Diterpenes of Flowering Plants

Compositae (Asteraceae)
Springer-Verlag
New York Berlin Heidelberg
London Paris Tokyo Hong Kong
Fred Seaman Christa Zdero
Drug Dynamics Institute Institute of Organic Chemistry
College of Pharmacy Technical University
The University of Texas D-1000 Berlin 12
Austin, Texas 78712, USA Federal Republic of Germany
Ferdinand Bohlmann Tom J. Mabry

Institute of Organic Chemistry Department of Botany
Technical University The University of Texas
D-1000 Berlin 12 Austin, Texas 78712,USA
Federal Republic of Germany
Cover: The plant illustrated is Ageratina gypsophylla B. Turner, a localized endemic species of Nuevo
Leon, Mexico. Ageratina species produce both the acyclic geranylnerol-type and bicyclic ent-Iabdane
diterpenes shown on the cover (in the background). The illustration is provided by B. Turner.
Library of Congress Cataloging-in-Publication Data

Diterpenes of flowering plants/F. Seaman ... let al.].
p. cm.
Contents: Compositae (Asteraceae)
Includes bibliographical references.
ISBN-13:978-1-4612-7945-7 e-ISBN-13:978-1-4612-3274-2
DOl: 10.1 007/978-1-4612-3274-2
1. Diterpenes. 2. Angiosperms-Composition. 3. Angiosperms-Classification. 4. Botanical
chemistry. 5. Plant chemotaxonomy.
I. Seaman, F. (Fred)
QK898.T4D57 1989
582. 13 '04 I 92-dc20 89-21877
Printed on acid-free paper
© 1990 by Springer-Verlag New York Inc.

Softcover reprint of the hardcover 15t edition 1990
All rights reserved. This work may not be translated or copied in whole or in part without the written
permission of the publisher (Springer-Verlag, 175 Fifth Avenue, New York, New York 10010,
U.S.A.), except for brief excerpts in connection with reviews or scholarly analysis. Use in
connection with any form of information storage and retrieval, electronic adaptation, computer
software, or by similar or dissimilar methodology now known or hereafter developed is forbidden.
The use of general descriptive names, trade names, trademarks, etc. in this publication, even if the
former are not especially identified, is not to be taken as a sign that such names, as understood by the
Trade Marks and Merchandise Marks Act, may accordingly be used freely by anyone.
Typeset by Technical Typesetting Incorporated, Baltimore, Maryland.
987 654 3 2 I
ISBN-13:978-1-4612-7945-7
Contents
Chapter 1. Introduction ..................................... .
Chapter 2. Compound Names, Structures, and Sources ............ 3
11.1. Names of Reported Compounds . . . . . . . . . . . . . . . . . 3

11.2. Structures of Reported Compounds .............. 3
II. 3 . Plant Sources and References for Diterpenes ...... 6
Chapter 3. Biogenesis........................................ 385
111.1. ent- and Normal-Iabdanes ..................... 385

III.2. Tricyclic Diterpenes .......................... 388
I1I.3. Tetracyclic Diterpenes ........................ 389
I1I.4. Biosynthetic Evidence. . . . . . . . . . . . . . . . . . . . . . . .. 389
Chapter 4. Diterpene Distribution: Compositae ................... 431
IV.1. Subfamilial Distribution Patterns ................ 431

IV.2. Tribal Affinities ............................. 432
IV.3. Infrageneric Distribution Patterns ............... 434
Chapter 5. Biological Activity of Diterpenes ..................... 485
V. 1. Introduction ............................. . . .. 485

V.2. Linear Diterpenes ............................ 485
V.3. Bicyclic Diterpenes ........................... 485
V.4. Tricyclic Diterpenes .......................... 486
V.5. Tetracyclic Diterpenes ........................ 487
Chapter 6. Diterpene Analysis with Emphasis on Clerodanes ....... 493
VI.l. Clerodanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 493

V1.2. Other Bicarbocyc1ics . . . . . . . . . . . . . . . . . . . . . . . . .. 505
VI Contents
V1.3. Tricarbocyclics .............................. 505

VI.4. Tetracarbocyclics and Related Skeletons. . . . . . . . .. 506
Chapter 7. References ....................................... 551
Appendix Alphabetical Listing of Molecular Substituents

including Ester Sidechains .......................... 579
Indexes 591
CHAPTER 1
Introduction
More than 1200 diterpenes have been identified from approximately 550
Compo sitae taxa (Figure 1 [pp. 219-384], Tables 1-3 [pp. 7-218]). The annual
output of such reports rose sharply during the past several years, a trend that was
also reflected by other major lipophilic constituents of the Compositae:
acetylenes (63, 465), sesquiterpene lactones (266, 458), and benzofurans and
chromenes (429). Unlike these other natural products, no review of the
diterpene chemistry of the Compositae has been published. Given the bulk of
data currently on hand, a review of this topic is clearly overdue.
Several major goals influenced the preparation of this review. The first was to
provide a useful reference to guide terpenoid chemists to the literature of known
compounds. The published reports for 1200 structures provide a sizable body of
spectroscopic data applicable to the investigation of new compounds.
The study of diterpenes has been hampered by the absence of an all-inclusive
nomenclature and classification system for the various skeletal types. Conse-
quently, a second goal was to organize structural data into a classification
scheme designed to group compounds by biogenetic homology, and to
standardize such features as diterpene nomenclature and numbering. Pursuant to
this goal, the published names (Table 1) and numbering systems (Table 2) for all
compounds are included.
The third goal was to compare the distribution of diterpenes to the
classification scheme used to subdivide the Compositae into its subfamilies,
tribes, subtribes, genera, etc., and to seek chemical distribution patterns that
paralleled the plant taxonomic boundaries. As diterpenes constitute a substantial
body of raw taxonomic data, they may hold some promise as novel characters
for use in plant taxonomy.
The fourth goal was to critically review the quality of published structure-
elucidation arguments. As will be discussed in detail (Chapter six), eagerness to
describe novel compounds in absolute stereochemical terms has led to much
confusion, particularly in the description of new clerodane structures. The
lengthy review of this topic hopefully will aid in the proper assessment of
stereochemical assignments.
The fifth goal was to develop a computerized diterpene database from which
2 1. Introduction
this review's tables could be extracted. Major topics dealt with in each chapter
represent some facet of programmed access to the diterpene database.
Accomplishing this final goal simplifies the future updating of this review by
automating the process of compiling up-to-date tabular information (e.g., Tables
1-3).
Diterpene data for the Compositae are included in Tables 1-3 (Chapter 2). In
Table 1, the compound names and numbers are grouped according to
membership in one of lO3 different skeletal types and listed alphabetically within
the skeletal-type group. Table 2 lists for each skeleton the compound numbers
and associated molecular descriptions, while Figure 1 displays the correspond-
ing structures. Table 3 lists all compound numbers and the Compositae taxa
from which the compounds were reported together with the reference numbers
corresponding to these reports. Distributional data were extracted from the
literature and from the authors' unpublished results. Alphabetized lists of
compound names and species appear in the Index together with citation page
numbers.
In the discussion of diterpenoid biogenesis (Chapter 3), each skeletal type is
described in terms of its likely mode of origin along one of two routes, the ent-
labdane-based route or the normal-Iabdane-based route. Hypothetical biogenetic
schemes for most skeletons are illustrated. Next, compound distribution is
discussed in terms of patterns of structural variability found at different plant
taxonomic levels (Chapter 4). Interspecific variation is detailed using six genera
(Brickellia, Stevia, Baccharis, Helichrysum, Helianthus and Montanoa)
representing the major diterpene-producing tribes of the Compositae. The next
chapter (five) describes the biological activities associated with different
diterpene skeletal types. The last chapter reviews the analytical methods used to
identify diterpenes and provides an interpretation of spectroscopic data for
several types, principally the clerodanes.
CHAPTER 2
Compound Names, Structures, and

Sources
II. 1. Names of Reported Compounds

The names (Table 1 [pp. 7-59]) and structures (Figure 1 [pp. 219-384]) of
diterpenes reported from the Compositae are organized according to skeletal
type following the sequence indicated in Figure 2 (p. 392). If a name was
assigned to a structure at the time the compound was reported, that name was
included in Table 1. Otherwise, the structure was given a name compatible with
the names previously assigned to related compounds. If more than one name was
applied in the literature to the same structure, usually the first-published name
was included in Table 1, followed by additional names listed within brackets.
The compound number listed with each name was used throughout this treatment
when reference to the compound was made. Comments about a reported
compound were also included in brackets on a line below the compound name.
Usually these comments describe situations in which the name applied to the
compound was incompatible with either the illustrated structure or the published
spectroscopic data.
n.2. Structures of Reported Compounds

An alternative database-generated method of diterpene structure representation
introduced in Table 2 (pp. 60-149) departs from the traditional approach using
the "R-group" system for differentiating related compounds. The rationale for
developing an alternative method is that by using it, a computer-generated set of
structures (e.g. an expanded Table 2 contained within a future update of this
review) can easily be produced from the diterpene database, even when the
database has grown to many times its present size. The alternative insertion of
many "R-group" -style structure illustrations into an updated version of Figure 1
would be prohibitively time consuming. Thus, illustrating structures in updates
of this review will be handled by this alternative method.
11.2.1. Structure Description Codes

In Table 2, diterpene structures are identified by compound number and grouped
with related structures belonging to the same skeletal type. The structural
4 2. Compound Names, Structures, and Sources
information given for each molecule (Table 2), together with the accompanying
carbocyclic (or in some cases heterocyclic) skeleton, are sufficient to derive the
compound's constitution and stereochemistry. By superimposing on the skeleton
the substituents listed in the molecular description code, a molecule can be
constructed with as much structural information as was included in the original
report. In the molecular description, each substituent code is separated by
semicolons within a string that begins with double bond substituents, proceeds
through various oxygen substituents, and ends with hydrogens:
I. Double Bonds
Double bonds are always indicated by a two-center code (e.g., 3(4), 9(11) that
identifies the two carbons linked by the double bond. If double bonds occur
within the ring system, the steric relations around the double bond are defined by
the skeleton illustrated with the description. Thus, for each cyclic double bond
the steric relationship (Z or E) of the ring carbons attached to the doubly bonded
carbons is defined by the relationship indicated in the illustrated skeleton.
For linear diterpenes or the linear segments of cyclic compounds with
ambiguous double bond stereochemistries, the steric relationship about the
double bond is indicated by a Z or E suffix (e.g., 13(14)E, 2(3)Z). The Z or E
assignment results from the comparison of the sequence-rule-preference of the
four atoms attached to the doubly bonded carbons (as specified in Rule E-2.2. of
the IUPAC Rules for Nomenclature of Organic Chemistry). Several examples of
Z and E assignment are discussed below in order to familiarize the reader with
this method.
II. Oxygen Functionalities

A. Carboxyls: If present, the first-listed oxygen substituent is the
carboxyl function (e.g., 19(=0,OH». This code assigns a carbonyl group
(=0) and a hydroxyl group (OH) to a specific center, carbon number 19. In
compounds containing a lactone function, this carboxyl code is replaced by a
single carbonyl group code (e.g. 19(=0» and a separate string-entry indicating
the position and orientivity of the oxido linkage (e.g., 19(-0-)6,6).
B. Ketones and Aldehydes: Ketones and aldehydes are denoted by the
carbonyl group code, (=0), associated with a secondary (ketone) or primary
(aldehyde) carbon of the skeleton (e.g. 3(=0».
C. Hydroxyls, Esters, etc.: Hydroxyls are indicated by a code, (OH) ,
that is preceded by the number of the carbon to which it is attached and the
orientation (ex or (6) ofthe attachment (e. g., 6,6 (0 H». Esters and other attached
groups are specified in the same fashion, using approximately 80 different codes
corresponding to the attached organic acid, etc. (e.g. 7ex(OAng), 2,6(OAc». The
Appendix lists the codes and structures for these attached groups. If attachment
is through an oxygen, this is indicated in the code. For example, the codes for an
acetate group and an acetyloxy substituent are respectively (Ac) and (OAc).
D. Epoxides, Ether- or Oxido-Linkages, etc.: Epoxides and other oxido-
bridges are indicated by a code (e.g. 3,6(-0-)4,6) specifying the two centers of
attachment and, if known, the orientivity of attachment.
Structures of Reported Compounds 5
III. Hydrogens
Hydrogens are included in order to define the orientivity (R or S) at a chiral
center. For example, the entry, 8!3(H), in reference to a labdane diterpene
defines the orientation of the attached ring-methyl at C-8 as being alpha (a):
12 14
18 II
If no substituent is indicated for an available point of attachment at a skeletal

carbon, then the presence of hydrogen(s) at that position is implicit.
2.2.2. Examples of Molecular Descriptions

I. Linear diterpene example: 15, 19-dihydroxy-14-oxo-geranylnerol
Skeleton (No.1. Geranylnerol):
11 11 20
Molecular description:
1004 2(3)Z;6(7)Z; lO(11)E; 14( =0); l(OH); 15(OH); 19(OH)
Because the skeleton immediately preceding the compound number 1004
description lacks double bonds, it is necessary to include in the molecular
description the steric relationships about each of the three double bonds. The
first double bond occurs at C-2-C-3 and according to sequence-rule-preference,
the "Z" suffix stipulates that C-1 and C-4 occur on the same side ofthe·double
bond. The "Z" suffix of the C-6-C-7 double bond requires that the two
sequence-rule-preferred groups on this double bond, the hydroxymethylene

function (C-19) and C-5 (and its associated ligands), occupy the same side of the
double bond. The "E" suffix of the 1O,1l-double bond indicates that, because
C-9 and C-12 and their associated ligands are the sequence-rule-preferred
groups, they must be on opposite sides of the double bond.
The remainder of the description indicates that a carbonyl group is located at
C-14 and hydroxyl groups are located at C-l, C-15, and C-19.
II. Bicyclic example: 14{:l-Carterothamnotriol-15-0-acetate

Skeleton (No. 16. "Normal"-labdane):
12 14
II It
Molecular description:
95 12(13)E;9a(OH); 14{:l(OH); 15(OAc);8a(H)
The skeleton immediately above this description of compound number 95

possesses a six-carbon sidechain into which the single double bond must be
inserted. Because this sidechain is not part of the cyclic portion of the molecule,
the molecular description code, 12(13)E, includes an "E" defining the steric
relationship around the double bond. Thus, sequence rule-preferred C-11 and C-
14 are situated on opposite sides of the double bond.
The next three entries, 9a(OH), 14{:l(OH), and 15(OAc), indicate the
placement of an a-oriented hydroxyl group at C-9, a {:l-oriented hydroxyl group
at C-14 and an acetate at C-15. The presence of an a-oriented H-14 is implicit in
the placement of a (:l-hydroxyl at C-14.
The code, 8a(H), defines the orientivity about C-S. In this case, it dictates {:l-
orientation for the C-8 methyl group.
II.3. Plant Sources and References for Diterpenes

Table 3 (pp. 150-21S) lists all diterpene compound numbers, the species of the
Compositae from which they were reported and the reference numbers for the
reports. Species names complete with authorities are listed alphabetically in the
Species Index.
Table 1. Compound Numbers and Names 7
TABLE 1. Compound numbers and names of diterpenes from the Compo sitae
(Asteraceae) .
Compound:
No. Name
I. Linear or Unicarbocyclic
1. Geranylnerol
1 Geranylnerol
2 Geranylnerol, 18-hydroxy-
3 Geranylnerol, 20-hydroxy-
4 Geranylnerol, 17,20-dihydroxy-
5 Geranylneral
6 Wyethic acid
7 Geranylnerol, 19-hydroxy-13-oxo-
8 Geranylnerol, 12,20-dihydroxy-16-oxo-
14 Viguieric acid [(2Z,6Z,10E)-3,15-dimethyl-7-carboxy-11-
formyl-2,6,10,14-hexadecatetraen-1-o1)
15 Geranylnerol, 12,20-dihydroxy-19-acetoxy-
984 Geranylnerol, 19-acetoxy-20-hydroxy-
948 Geranylnerol, 8,12,19-trihydroxy-
949 Geranylnerol-6,7-epoxide, 8,12,19-trihydroxy-
978 Geranylnerol, 19-hydroxy-12-oxo-
979 Geranylnerol, 6,7-epoxy-19-hydroxy-12-oxo-6,7-dihydro-
1002 Geranylnerol-19-oic acid
1003 Geranylnerol-19-oic acid, 1-acetyl-
1004 Geranylnerol, 15,19-dihydroxy-14-oxo-
1005 Geranylnerol acetate, 19-acetoxy-15-hydroxy-14-oxo-
1020 Geranylnerol, 20-acetoxy-10,11-epoxy-10,
11-dihydro-9-hydroxy-
1095 Zoapatanol, pre-
1096 Tomexanthol, pre-
1111 Gerany1nerol, 12-oxo-
TABLE 1. (contd.)
Compound:
No. Name
1112 Gerany1nerol, 18,19-diacetoxy-17,20-dihydroxy-
1113 Geranylnerol, 18,19,20-triacetoxy-17-hydroxy-
1114 Geranylnerol, 18-acetoxy-17,20-dihydroxy-
1115 Geranylnerol, 19-acetoxy-17,20-dihydroxy-
1117 Geranylnero1, 9,17,19-trihydroxy-
2. Geranylgeraniol
11 Geranylgeraniol, 12,19-dihydroxy-
12 Geranylgeraniol acetate, 12,19-dihydroxy-
13 Geranylgeraniol, 16-hydroxy-
16 Geranylgeraniol, 14,
15-dihydro-4, 14, 15-trihydroxy-
17 Geranylgeranial
18 Geranylgeranial, 4-hydroxy-
19 Koanoadmantic acid
20 Geranylgeraniol,13-oxo-2,3-dihydro-
21 Geranylgeranjo1, 19-hydroxy-12-oxo-10,11-dihydro-
22 Geranylgeraniol, 12,18-dihydroxy-6,7Z-
954 Hexa-deca-2E,6E,10E,14-tetraene, I-hydroxy-11-carboxy-3,
7, 15-trimethy1-
1118 Gerany1geranio1, 17-hydroxy-18-acetoxy-
1119 Geranylgerana1, 12-oxo-
1120 Aspiliaparviol
3. Geranyllinalool
23 Geranyllinalool
24 Gerranyllinalool, 13-hydroxy-
25 Geranyllina1oo1, 13-acetoxy-
26 Geranyllinalool, 9-hydroxy-
27 Geranyllinaloo1, 9-acetoxy-
28 Geranyllinalool, 5-hydroxy-
TABLE 1. (contd.)
Compound:
No. Name
29 Geranyllinalool, 9-acetoxy-5-hydroxy-
30 Geranyllinalool, 5,9-diacetoxy-
31 Geranyllinalool, 13-acetoxy-5-hydroxy-
32 Geranyllinalool, 12-oxo-
33 Geranyllinalool, 13-oxo-
34 Geranyllinalool, 13-oxo-14,15-epoxy-
35 Geranyllinalool, 15-hydroxy-13,14-dehydro-14,15-dihydro-
36 Geranylinalool, 14,15-dihydro-13,14,15,16-teradehydro-
37 Geranyllinalool, 14,15-dihydro-14,15-dihydroxy-
38 Geranyllinalool, 5,14,15-trihydroxy-14,15-dihydro-
39 Geranyllinalool, 14,15-dihydroxy-9-acetoxy-14,15-dihydro-
1121 Geranyl linlol, 13-acetoxy-
1122 Geranyl linalol, 12-oxo-10,11-dihydro-
1123 Geranyl linalol, 12-oxo-15-hydroxy-13,14E-dehydro-
10, 11,14, 15-tetrahydro-
4. Phytol-Derived
59 Neophytadiene
80. 14-Methylgeranylnerol
9 Geranylnerol, 12,19,20-trihydroxy-14-methylene-
10 Geranylnerol, 12,20-dihydroxy-19-acetoxy-14-methylene-
980 Smallantha-2Z,6Z,10E,13E-tetraene, 1,19-dihydroxy-
981 Smallantha-2Z,10E,13E-triene,
1, 19-dihydroxy-6,7-epoxy-12-oxo-
982 Smallantha-2Z,6Z,10E,14(21)-tetraene, 1,
19-dihydroxy-12-oxo-
983 Smallantha-2Z,10E,14(21)-triene, 1,
19-dihydroxy-6,7-epoxy-12-oxo-
1094 Tomentol, pre-
5. Acanthoaustralane
TABLE 1. (contd.)
Compound:
No. Name
40 Acanthoaustralide
41 Acanthoaustralide-1-0-acetate
42 Acanthoaustralide, 17-hydroxy-
43 Acanthoaustralide, 17-acetoxy-
1124 Acanthoaustra1ide, 1,6-diacety1-
6. Acanthoaustralane-6,11-Epoxide
44 Me1fusanolide, 1,10-dihydroxy-17-acetoxy-
45 Melfusanolide, 1,lO,17-trihydroxy-
7. Isoacanthoaustralane
46 Isoacanthoaustralide, l7-hydroxy-
47 Isoacanthoaustralide, l7-acetoxy-
48 Isoacanthoaustralide-l-O-acetate
[According to illustrated structures, 46 and 47 were
assigned an orientation at 2(3) opposite to the one assigned
earlier to 48. No revision of 48 was indicated in the later
publication.]
8. Geranylgeraniol-18,8-Lactone
49 Ichthyouleolide
50 Ichthyouleolide, 19-acetoxy-
51 Ichthyouleolide, l5-peroxy-13,14t-dehydro-14-l5-dihydro-
52 Ichthyouleolide, l5-hydroxy-13,14t-dehydro-14-l5-dihydro-
53 Ichthyouleolide, 14-peroxy-15,17-dehydro-14,15-dihydro-
54 Ichthyouleolide, 14-hydroxy-15,17-dehydro-14,15-dihydro-
9. Oxepane
55 Zoapatanol
56 Tomexanthin
57 Montanol
1097 Tomentol
TABLE 1. (contd.)
Compound:
No. Name
1098 Tomexantho1
1099 Tomentano1
86. Melcanthane
1006 Me1cantho1ide, 1,6,7-trihydroxy-17-acetoxy-
10. Mikanofurane
58 Mikanifuran
11. Centipedane
60 Centipedic acid
61 Conypododiol
1125 Furoso1idagonone
1126 Furoso1idagono1
1127 Furosolidagonone, 13-hydroxy-
1128 Furoso1idagonone, 15-peroxy-13,14E-dehydro-14,15-dihydro-
62 Dimeroperatic acid
63 Dimeroaperatate, methyl-
64 Dimerobrasiolide
1129 Furosolidagonone, l-oxo-2,3-dehydro-1,2,3,20-tetrahydro-
1130 Gutieso1brio1ide, 17-hydroxy-
1131 Gutiesolbriolide, 10E-17-hydroxy-
1132 Gutiesolbriolide, 17-acetoxy-
1133 Geranylgeraniol-20-acid lactone, 17,19-dihydroxy-18-acetoxy-
6,7,10,11-tetrahydro-
1134 Geranylgeraniol-20-acid lactone, 17-hydroxy-18,19-diacetoxy-
6,7,10,II-tetrahydro-
1135 Gutiesolbriolide, 17-hydroxy-iso-
1136 Gutieso1briolide, 17-acetoxy-iso-
TABLE 1. (contd.)
Compound:
No. Name
1137 Furosolidagonone, 20-oxo-1,2-epoxy-1,2,3,20-tetrahydro-
13. Geranylterpinene
65 Helicallen-16-ol
66 Helicallen-16-al
67 Helicallen-16-oic acid, 14,15-dihydro-
68 Geranyl-a-terpinene, 9-
69 Geranyl-a-terpinene, 10,11H-10,11-dihydroxy-9-
70 Geranylcurcumen,9-
71 Geranylcurcumen, 10,11H-10,11-dihydroxy-9-
[Compounds 69 and 70 were named "1l,12H-ll,12-dihydroxy- .•. "
derivatives, but this numbering was incompatible with
illustrated structures and previously published homologous
compounds. 1
72 Geranylascaridol, ~-10,11H-10,11-dihydroxy-9-
1101 Geranylascaridol, a-10,11H-10,11-dihydroxy-9-

1138 Geranyl-a-terpineol, 9-
14. Isocembrene
73 Isocembrene, 15-hydroxy-13,18H-
15. Geranylnerol-11,14-a-Epoxide
74 Ligantrol
75 Ligantrol-monoacetate
II. Norma1-Bicarbocyc1ics and Derivatives

16. Norma1-Labdane
76 Labda-8(17)-13-dien-15-ol
1103 Labd-13-ene, 8a,15-dihydroxy-
77 Acanthospermol-~-galactosidopyranoside
78 Labda-8(17),13-diene
Table I. Compound Numbers and Names 13
TABLE 1. (contd.)
Compound:
No. Name
80 Gymnospermin
79 Labdan-8a,15-diol
81 Labdan-8a,15-diol, 13-epi-
[In published structure, C-5-H was shown as ~-oriented.)
82 Carterothaminotriol
83 Carterothaminotriol-15-0-acetate
84 Carterothaminotrio1-14,15-0-diacetate
85 Labd-8(17)-ene, 15-hydroxy-13,14-epoxy-
[In the published name, this compound was called " .•. 14,15-
epoxy- ... ".)
86 Labd-7-ene, 13R,14R,15-trihydroxy-
87 Labd-(8,9)-ene, 13R,14R,15-trihydroxy-
88 Labd-8(17)-ene, 14,15-dihydroxy-
89 Labd-8(17)-ene, 13,14,15-trihydroxy-
90 Labd-8(17)-ene, 15-acetoxy-14-hydroxy-
993 Labd-7-ene, 3a,15-dihydroxy-
994 Labd-7-ene, 15-[2-methylbutyryloyloxy)-3a-hydroxy-
995 Labd-8(17)-ene, 3a,7a,15-trihydroxy-
91 Labd-8(17)-ene, 15-acetoxy-13,14-dihydroxy-
92 Labd-8(17)-ene, 14-acetoxy-15-hydroxy-
93 Labd-8(17)-ene, 15-acetoxy-13-hydroxy-14-propiony1oxy-
94 Carterothamnotriol, 14~-
97 Brickellidiffusic acid angelate

98 Cativic acid, 2a,3a-[angeloyloxy-&
2-hydroxy-2-methylbutyryloxy)-7a-trans-cinnamoyloxy-
99 Cativic acid, 2a,3a-[angeloyloxy- &
2-hydroxy-2-methylbutyryloxy)-7a-cis cinnamoy1oxy-
100 Cativic acid, 2-angeloyloxy-13,14Z-dehydro-
116 Labda-7,13Z-15-oic acid, 3a-hydroxy-
101 Cativic acid, 18-angeloyloxy-13,14-dehydro-
102 Cativic acid, 18-tigloyloxy-13,14-dehydro-
TABLE 1. (contd.)
Compound:
No. Name
103 Cativic acid, 3a-angeloyloxy-2a-hydroxy-13,14Z-dehydro-
104 Cativic acid,3a-trans-cinnamoyloxy-2a-hydroxy-13,
14Z-dehydro-
105 Cativic acid, 3a-cis-cinnamoyloxy-2a-hydroxy-13,
14Z-dehydro-
106 Cativic acid, 3a-angeloyloxy-2a-hydroxy-(13Z)-13,
14-didehydro-
[Compound 106 is identical to 103.]

14-didehydro-
14-didehydro-8(17)-
109 Cativic acid, 2a-ange1oy1oxy-3a-hydroxy-(13Z)-13,
14-didehydro-8(17)-
110 Batudioic acid
111 Labda-8(17),13E-dien-1s-oic acid
112 Labda-7,13E-dien-1s-oic acid, 2a-tig1oy1oxy-
113 Sempervirenic acid [3~-acetoxy-1abda-7,13-dien-1s-oic acid]
114 Labda-[7.13E-dien]-ls-oic acid, 3a-hydroxy-
115 Labda-[7.13E-dien]-ls-oic acid, 3~-hydroxy-
958 Labdan-1s-oic acid, 8a-hydroxy-

117 Labda-7,13E-dien-1s-oic acid, 3-oxo-
118 Cativic acid
991 Cativic acid, 3a-hydroxy-
992 Cativic acid methyl ester, 3a-hydroxy-
119 Labda-7-en-1s-oic acid, 3a-hydroxy-
120 Labda-7-en-1s-oic acid, 3~-hydroxy-
360 Labdane, (-)-7~,8a,ls-trihydroxy- [Gymnospermin]

121 Labdano1 acid
871 Labd-7-en-2a,ls-diol, 13 -
872 Labd-7-ene, 2a-hydroxy-1s-[3,4-dihydroxycinnamoy1oxy]-13 -
873 Labd-7-ene,2a-hydroxy-1s-
[4-hydroxy-3-methoxy-cinnamoy1oxy]-13 -
TABLE 1. (contd.)
Compound:
No. Name
874 Labd-7-ene, 2a-hydroxy-15-[4-hydroxy-cinnamoyloxy)-13 -
122 Cativic acid, 18-angeloyloxy-
123 Cativic acid, l8-tigloyloxy-
[Published names for 122 and 123 indicated that they were C-
19-substituted, but the illustrated structures and reference
to the substituents' axial orientation are compatible only
with a C-18-substituted structure.]
124 Cativic acid, 2a,3a-dihydroxy-
125 Cativic acid, 2a-hydroxy-3a-[2-hydroxy-2-methylbutyryloxy]-
126 Cativic acid, 3a-angeloyloxy-2a-hydroxy- [Brickellia acid C]
127 Cativic acid, 3a-trans-cinnamoyloxy-2a-hydroxy-
128 Cativic acid, 3a-cis-cinnamoyloxy-2a-hydroxy-
129 Cativic acid, 3-oxo-
870 Labd-7-en-1S-oic acid, 3~-hydroxy-2a-senecioy1oxY-13 -
130 Agathenic acid, 8,17H-7,8-dehydro-
977 Labd-8(17)-en-15-al-19-oic acid
131 Agathenic acid, 8,17,13,14H-7,8-dehydro-
132 Biformene, 12,13E-
133 Biformene, 3a-hydroxy-12,13E-
134 Biformene, 3~-hydroxy-12,13E-
135 Biformene, 3~-acetoxy-12,13E-
136 Biformene, 3-oxo-12,13E-

959 Labd-8(17)-en-15-oic acid, 2~-acetoxy-
137 Communic acid

1104 Labd-8(17),12E,14-trien-19-oic acid
138 Communic acid, 7a-acetoxy-trans-
139 Abienol
140 Abienol, 7j3-hydroxy-
141 Nidorellol
142 Nidorellol, 6a-hydroxy-
143 Nidorellol, 6a-anqeloyloxy-
TABLE 1. (contd.)
Compound:
No. Name
144 Abienol, 6~-hydroxy-12E-
145 Abienol, 7~-acetoxy-12E-
146 Abienol, 6~,7~-dihydroxy-12E-
147 Abienol, 6~,18-dihydroxy-12E-
148 Abienol, 7~-acetoxy-6~-hydroxy-12E-
149 Aristin-19-0-arachinate, l~-acetoxy-
150 Aristin-19-0-coumarate, l~-acetoxy-
151 Aristin-19-0-cis-coumarate, l~-acetoxy-
152 Labda-12(El,14-diene, 9a,19-dihydroxy-

153 Sclareol, 6a-angeloyloxy-
[Published structure contained a C-6~-oriented angelate,
contradicting the published name.)
1102 Sclareol
996 (+l-Manool
1105 Manool, iso-
1106 Manoo1, 3S-hydroxy-iso-
1107 Manool, 3-oxo-iso-
154 Salicifoliol
[Absolute stereochemistry not indicated.)
155 Abienol, iso-
156 Abienol, 7~-acetoxy-6~-hydroxy-12~-peroxiiso-
157 Abienol, 7~-acetoxy-6~-hydroxy-12a-peroxiiso-
158 Solidagenone
159 Lambertianic acid, 17-hydroxyiso-
160 Gutierrezianol acid-[2'-methylbutyrate)
161 Gutierrezianol acid-isobutyrate
162 Gutierrezianol acid-isovalerate
163 Lambertianic acid, 7a-hydroxy-
1021 Austroinulin-7-0-acetate, (12Zl-6-desoxy-
1022 Abienol, 6a-hydroxy-7~-acetoxy-12E-
TABLE 1. (contd.)
Compound:
No. Name
1023 Austroinulin-7-0-acetate, (12Z)-
1024 Labdenol acid, (13Z)-
1139 Labdan-8a,15-diol, 13~-H-
1140 Cordobic acid (7a,18-Dihydroxylabd-8(17)-en-oic acid]

1141 Cordobic acid 18-acetate
1142 Cordobic acid, 7-epi-
1143 Salvic acid
1144 Salvic acid, 7a-acetyl-
1145 Discoidic acid (4~-hydroxymethyllabd-7-en-15-oic acid]
1147 Labd-8(17),12E,14-trien-19-oic acid
96 Gutierrezia sphaerocephala labdane-a-L-arabinopyranoside 1
97 Gutierrezia sphaerocephala labdane-a-L-arabinopyranoside 2
1148 Gutierrezia sphaerocephala labdane-~-D-arabinopyranoside 3
1151 Abienol, 3~-acetoxy-iso-
1152 Gnaphala-13(16),14-diene, 8a-hydroxy-
17. Grinde lane

165 Grindelic acid, 7a-hydroxy-7, 8-dihydro-8 (17)-dehydro-
166 Grinde-6,8(17)-dienic acid
167 Grindelic acid
168 Grindelic acid, 1a-hydroxy-
169 Grindelic acid, 3~-hydroxy-

172 Grindelic acid, 6~-hydroxy-
173 Grindelic acid, 17-hydroxy- (Oxygrindelic acid]

171 Grindelic acid, 6a-formyloxy-
174 Grindelic acid, 17-acetoxy-
175 Grindelic acid, 17-propiony1oxy-
TABLE 1. (contd.)
Compound:
No. Name
176 Grindelic acid, 17-isobutyry1oxy-

177 Grindelic acid, 17-isova1ery1oxy-
178 Grindelic acid, 17-[2-methy1butyry1oxy)-
179 Grindelic acid, 17-methoxy-
180 Grindelic acid, 19-hydroxy-
181 Grindelic acid, 19-acetoxy-
182 Grindelic acid, 19-isova1eryloxy-
183 Grindelic acid, 19-isobutyryloxy-
184 Grindelic acid, 19-[2-methylbutyryloxy)-
185 Grindelic acid, 19-succinyloxy-
186 Grindelic acid, 19-oxo-
187 Grindelic acid, 19-oic-
188 Grindelic acid, 18-hydroxy-
189 Grindelic acid, 6-oxo-
190 Grindelic acid, 19-acetoxy-6-oxo-
191 Grindelic acid, 7~,8~-epoxy-7,8-dihydro-
192 Grindelic acid, 7a,8a-epoxy-7,8-dihydro-

955 Grindelic acid, iso-
956 Grindelic acid, 17-grindeloxy-
193 Solidagenone, 9-dehydroxy-9a, 13a-epoxy-13, 16-dihydro-
194 Solidagenone, 13-epi-dehydroxy-9a, 13a-epoxy-13, 16-dihydro-
1036 Grindelic acid, 7~-hydroxy-8(17)-dehydro-7,8-dihydro-
1060 Grindelic acid-15-0-arabinoside

1153 Grindelate, methyl-
1187 Grindelic acid 15-0-arabinoside
[Incorrectly illustrated as an ent-labdane]
18. Normal-Labdane-8,13-Epoxide
272 Manoyl oxide
TABLE 1. (contd.)
Compound:
No. Name
195 Jhanol
196 Jhanol acetate
197 Jhanidiol
19S Jhanidiol-19-monoacetate
199 Jhanidiol-diacetate
200 Manoyl oxide, 3~-hydroxy- [1S-deoxylazarcardenasol]
201 Manoy1 oxide, 1S-benzoyloxy-3~-hydroxy-
[1S-benzoyloxylarcardenasol]
964 Manoyl oxide, 15-oxo-14,15-dihydro-
273 Manoyl oxide, 13-epi-
202 Manoyl oxide, 1S-hydroxy-l3-epi-
[Published structure was shown with a C-1S substituent but
given a name indicating C-19 substitution. Reference to the
substituent's axial orientation indicates a C-1S
substituent.]
19. Norma1-Labdane-8,12-Epoxide
203 Carterochaetol, 16-hydroxy-

204 Carterochaetol, 16-acetoxy-
205 Carterochaetol acetate, 16-acetoxy-
206 Carterochaeto1, 16-oxo-
207 Carterochaeta1, 16-oxo-
20S Carterochaeto1, 16-hydroxy-13,14H-13a,14a-epoxy-
209 Carterochaeto1, 16-hydroxy-13,14H-13~,14~-epoxy-
210 Carterochaeto1
211 Carterochaeta acid
212 Carterochaeta1, 16-oxo-13,14H-12,13-dehydro-
213 Carterochaetal, 16-acetoxy-14-oxo-13,14H-12,13-dehydro-
20. Normal-Labdane-15,16-Lactone
164 Agathenic acid-16-1actone, S,17H-7,S-dehydro-
965 Labda-7,13-dien-15-acid-16-1actone, 17-hydroxy-
TABLE 1. (contd.)
Compound:
No. Name
966 Labda-7,13-dien-15-acid-16-1actone, 17-oxo-
214 Nidorella lactone
22. Normal-Labdane Spiroketal

215 Brickellidiffusic acid spiro ketallactone,
2a-angeloyloxy-17,O-dihydro-
216 Brickellidiffusic acid spiro ketal lactone,
2a-angeloyloxy-17a-hydroxy-17,O-dihydro-
217 Brickellidiffusic acid spiro ketal lactone,
2a-angeloyloxy-17~-hydroxy-17,O-dihydro-
218 Brickellidiffusic acid spiro ketal lactone, 2a-hydroxy-17,

O-dihydro-
938 Evillosin
23. Normal-Labdane, 7,8-Seco-

219 Koanolabda-12E,14-diene, seco-

220 Cativin-3,15-dioic acid, 3,4-seco-
25. Grindelane, 8,9-Seco-

223 Chrysothane [Strictanonic acid]
89. Grindelane, 19-Nor-

221 Grindelic acid, 4a-hydroxy-19-nor-
222 Grindelic acid, 4a-formyloxy-19-nor-
1154 Grindelate, methyl-4~-hydroxy-6-oxo-19-nor-
TABLE 1. (contd.)
Compound:
No. Name
26. Grindelane, 8,17-Bis-Nor-8,9-Seco-
224 Grindelistrictic acid
27. Normal-Labdane-20,12-Lactone, 5,10-Seco-

225 Nidorella lactone, seco-
226 Nidorella lactone-6-0-angelate, seco-
227 Nidorella lactone-6-0-isobutyrate, seco-
228 Nidorella lactone-6-0-[2-methylbutyrate], seco-
229 Nidorella lactone-6-0-isovalerate, seco-
230 Nidorella lactone-6-0-angelate, 5-deoxy-5-hydroxy-5H-seco-
100. Norma1-Labdane, 14, 15-Bis-Nor-

1155 Labden-13-one, 14,15-bisnor-B-hydroxy-1lE-
1157 Sterebin A
1158 Sterebin B
1159 Sterebin c
1160 Sterebin D
101. Norma1-Labdane, 13,14,15,16-Tetra-Nor-

1156 Norambreinolide
87. Hexanor1abdane
941 Jhanilactone
28. Relhaniane
231 Relhania acid
232 Koanophy1lic acid B
233 Koanophyllic acid A
234 Koanophyllic acid C
TABLE 1. (contd.)
Compound:
No. Name
235 Koanophyllic acid D
[Absolute stereochemistry for the koanophyllic acid series
was unproven.]
29. trans-Normal-Clerodane
(No proven structures of this type)
30. Clerodane, 5,10-Seco-

255 Nidoreseda acid, seco- [Conyzic acid, strictic acid]
[Revised to 9a-methyl, = 573]
256 Nidoreseda acid methyl ester, seco-
[Revised to 9a-methyl, = 573 methyl ether]
31. cis-Normal-Clerodane
238 Solidago alcohol, 8-epi-
[Reported as 5~,10a-~-clerodane]
253 Nidorellalactone, iso-

[Reported as 5~,10a-trans-clerodanel
254 Nidorellalactone
[Reported as 5~,10a-trans-clerodanel
257 Clerodan-15-oic acid, 3,4-dehydro-cis-

258 Solidago lactone II [Elongatolide C]
259 Solidago lactone III
260 Elongatolide E [Solidagolactone VII]
261 Solidago lactone III, 3a,4a-epoxy-3,4-dihydro-
262 Solidago lactone V
263 Solidago lactone II, 2a-hydroxy- [Solidago virgaurea
compound 4a]
264 Solidago1actone III, 2a-hydroxy- [Solidago virgaurea
compound 4c]
265 Solidago lactone V, 2~-hydroxy-
266 Solidago lactone II, 3~,4a-dihydroxy-3,4-dihydro-
267 Solidago lactone III, 3~,4a-dihydroxy-3,4-dihydro-

TABLE 1. (contd.)
Compound:
No. Name
268 Solidagolactone II, 3-oxo-3,4-dihydro-
269 Solidagolactone III, 3-oxo-3,4-dihydro-
545 Elongatolide A [SolidagolactoneIV;
6~-hydroxy-solidagolactone]
546 Elongatolide B
551 Kolavenic-15-acid lactone, 2a,16-dihydroxy-3a,4a-epoxy-
[Revised from ~-ent-clerodane]
552 Kolavenic-15-acid lactone, 6~-angeloyloxy-16-hydroxy-3a,
4a-epoxy-
[Revised from trans-ent-clerodane]
553 Elongatolide D [Solidagolactone VI(structure no.555)]
988 Solidagolactone VIII
239 Solidagoic acid A
240 Solidago aldehyde
241 Solidago alcohol
242 Solidago glycol
243 Solidago dialdehyde
244 Solidagoic acid B
246 Solidago lactol
247 Solidago epoxylactol
270 Guteriolide
556 Kolavenic acid lactone, l6-hydroxy-3,4-epoxy-
[Structure was revised to Sa, lOa-cis]
557 Kolavenic acid lactone, 7~-angeloyloxy-16-hydroxy-3,
4-epoxy-
[Revised to Sa, lOa-cis]
1025 Kolavenool, 6~-acetoxy-2-oxo-
1062 Solidago gigantea compound I

1063 Solidago gigantea compound III
1064 Solidago gigantea compound IV
1065 Solidago gigantea compound V
1066 Solidago gigantea compound II
1067 Solidago gigantea compound VI
TABLE 1. (contd.)
Compound:
No. Name
1068 Solidago gigantea compound VII
271 Chrysolic acid
1083 Cleroda-3,13(14)-diene-15,16-olide, 6a,18-dihydroxy-cis-
1084 Cleroda-3,13(14)-diene-15,16-o1ide, 18,19-dihydroxy-cis-
1085 Cleroda-3,13(14)-diene-15,16:18,19-diolide, cis-
1086 Cleroda-3,13(14)-diene-15,16-o1ide,
18, 19-epoxy-19a-hydroxy-cis-
1087 Cleroda-13(14)-ene-15,16-o1ide, 3a,4:18,19-diepoxy-18~,
19a-dihydroxy-cis-
1088 Cleroda-13(14)-ene-15,16:18,19-diolide,
3a,4-epoxy-19a-hydroxy-cis- .
1089 Cleroda-13(14)-ene-15,16-o1ide,
3a,4:18,19-diepoxy-19a-hydroxy-cis-
1090 Cleroda-13(14)-ene-15,16-olide, 3a,4~,19a-trihydroxy-18,
19-epoxy-cis-
1091 Cleroda-3,13(14)-diene-15,16-olide-19-oic ester,
19-0-a-L-arabinopyranosyl-cis-
1092 Cleroda-3,13(14)-diene-15,16:18,6a-diolide,
2~,6a-dihydroxy-cis-
90. Tricycloclerodane
947 Tricyclosolidagolactone
III. Normal-Tricarbocyclics and Derivatives

32. Sandaracopimarane (Normal-Pimarane)
274 Sandaracopimaradiene
927 Sandaracopimar-8(14),15-diene, 7a-hydroxy-
928 Sandaracopimar-8(14),15-diene, 1~,7a-dihydroxy-
929 Sandaracopimar-8(14),15-diene, 7a-hydroxy-1~-acetoxy-
930 Sandaracopimar-8(14),15-diene, 1~-hydroxy-7a-acetoxy-
931 Sandaracopimar-8(14),15-diene, l~,lla-dihydroxy-
932 Sandaracopimar-8(14),15-diene, l~,lla-diacetoxy-

TABLE 1. (contd.)
Compound:
No. Name
933 Sandaracopimar-8(14),15-diene, l~,

lla-dihydroxy-7a-acetoxy-
934 Sandaracopimar-8(14),15-diene, 7a-hydroxy-l~,
lla-diacetoxy-
935 Sandaracopimar-8(14),15-diene, 1~,7a,11a-triacetoxy-
936 Sandaracopimar-8(14),15-diene, 1~,11a-diacetoxy-6,7-epoxy-
937 Sandaracopimar-8(14),15-diene, 1~,11a-diacetoxy-7-oxo-
275 Sandaracopimaradiene, iso-

276 Sandaracopimar-15-ene, 8~-hydroxy-
277 Sandaracopimar-15-en-6~,8~-diol
278 Sandaracopimar-15-en-8~-01, 6~-acetoxy-
279 Sandaracopimar-15-en-8~,11a-diol
280 Sandaracopimar-15-ene, 8~-hydroxy-11a-senecioyloxy-
281 Sandaracopimar-15-ene, 8~-hydroxy-11a-tiglinoyloxy-
282 Sandaracopimar-15-ene, 8~-hydroxy-11a-acetoxy-
283 Sandaracopimar-15-en-11-one, 8~-hydroxy-
284 Sandaracopimar-15-ene, 8~-hydroxy-12~-acetoxy-
285 Sandaracopimar-15-en-3~,18-diol
286 Sandaracopimar-15-ene, 8~,20-dihydroxy-
287 Sandaracopimar-15-ene, 20-hydroxy-8~,20-oxido-
288 Sandaracopimar-15-ene, 8~,11a,12~-trihydroxy-
289 Sandaracopimar-15-en-8~,12~-diol, 11a-acetoxy-

290 Sandaracopimar-15-ene, 8~,12~-dihydroxy-11a-senecioyloxy-
291 Sandaracopimar-15-ene, 8~,12~-dihydroxy-l1a-tiglinoyloxy-
292 Sandaracopimar-15-en-8~,11a-diol, 12~-acetoxy-
293 Sandaracopimar-15-en-8~,11a-diol,
12~-(p-hydroxycinnamoyloxy)-
294 Sandaracopimar-15-en-8~-ol, l1a,12~-diacetoxy-
295 Sandaracopimar-15-en-8~,
12a-diol, 11~-acetoxy-
296 Sandaracopimar-15-en-11-one. 86.

12a-dihydroxy-
TABLE 1. (contd.)
Compound:
No. Name
297 Sandaracopimar-15-en-11-one, 12~-acetoxy-8~-hydroxy-
298 Sandaracopimar-15-en-6~,8~,11a-triol
299 Sandaracopimar-15-en-8~,11a-diol, 6~-acetoxy-
300 Sandaracopimar-8 (14) ,15-dien-18-oic acid

301 Sandaracopimar-7,15-dien-18-oic acid
302 Sandaracopimar-8(14),15-dien-18-oic acid, 3~-acetoxy-
807 Trinervinol [Isopimara-8(14)-en-3~,15,16,17-tetrol)
303 Sandaracopimar-7,15-dien-18-oic acid, 3~-acetoxy-
921 Sandaracopimar-8(14)-en-19-oic acid, 6~,15,16-trihydroxy-
304 Palarosan, 3a-hydroxy-13-epi-

305 Palarosan, 9a-hydroxy-13-epi-
891 Pimar-15-en-8~-ol, 13-epi-
306 Sandaracopimar-7-ene, 3a,15,16-trihydroxy-13-epi-
[Revised to rosane structure, = 313; 168)
307 Sandaracopimar-7-ene, 9a,15,16-trihydroxy-
[Revised to rosane structure, = 314; 168)
308 Julslimtetrol
922 Sandaracopimar-8(14)-en-6~-D-glucoside, 15,16-dihydroxy-
923 Sandaracopimar-8(14)-ene, 6a,15,16,18-tetrahydroxy-
[Compounds 922 and 923 were illustrated with ~-oriented C-10
methyl groups.)
34. Cassane
310 Osteomuricone, 2a-hydroxy-
311 Osteomuricone, 1~,2a-dihydroxy-
312 Osteomuricone, 1~,2a-dihydroxy-15,16-dihydro-
35. Rosane
306 Palarosane, 3a-hydroxy
313 Palarosane, 3~-hydroxy-
314 Palarosane, 3~,18-dihydroxy- [Jesromotetrol)

TABLE 1. (contd.)
Compound:
No. Name
315 Pa1arosane, 3-oxo-
881 Rimuen-5~-ol, ent-
882 Rimuen-5~,18-dio1, ent-
883 Rimuen-18-y1 acetate, 5~-hydroxy-ent-
884 Rimuen-3a,5~-dio1, ent-

885 Rimuen-18-y1 tig1ate, 5~-hydroxy-ent-
886 Rimuen-3a,5~,18-trio1, ent-

887 Rosa-5,15-dien-3a,18-dio1
888 Rosa-5,15-dien-3a-y1 acetate, 18-hydroxy-
889 Rosa-5,15-dien-18y1 acetate, 3a-hydroxy-
890 Rosa-1(10),15-dien-18-oic acid
[Published structure indicated a C-19 acid, while the
published name and other data indicated a C-18 substituent.]
1161 Jesromotro1, 3~,19-diacetoxy-
1162 Jesromotro1, 3~-acetoxy-
36. Sandaracopimarane, 19-Nor-13-Epi-

309. Ju1s1imdio1one, nor-
37. Norma1-Abietane
316 Abietadien-2a-01 acetate
317 Abietadien-3~-ol, 7,13-
318 Abietadien-3-one, 7,13-
[Compounds 316-317 are probably artefacts of 8(9),13(14)-
abietadiene-type compounds.]
319 Ferrugino1
320 Inuroy1eano1
321 Roy1eanone
322 Roy1eanone, dehydro-
323 Roy1eanone, 7-acetoxy-
324 Roy1eanone, 7-keto-
TABLE 1. (contd.)
Compound:
No. Name
1072 Junceanol W
1073 Junceanol X
1074 Junceanol Y
1163 Turbinatone
94. Stevisalane
1026 Stevisalicinone
IV. Normal-Tetracarbocyclics
73. Normal-Stachane
325 Cupressen-18-oic acid
[= 774?]
V. ent-Bicarbocyclics and Derivatives

38. ent-Labciane
326 ent-Labda-8(17),13-dien-15-o1
848 ent-Labda-8(17),13-dien-1S-ol, 2a-hydroxy-
327 ent-Labda-8(17),13-dien-15-0-bernsteinoate
849 ent-Labda-8(17),13-dien-15-o1, 2-oxo-
328 ent-Labda-8(17),13,14E-dien-15-o1, 7~-acetoxy-
844 ent-Labda-8(17),13E-diene, 3a-angeloyloxy-15,18-dihydroxy-

329 ent-Labda-8(17),13E-dien-15-o1-18-oic acid
[Viscidic acid A]
330 ent-Labda-8(17),13E-dien-15-acetoxy-18-oic acid
[Viscidic acid B]
331 ent-Labda-8(17),13E-dien-15-al, 2a-hydroxy-
332 ent-Labda-8(17),13Z-dien-15-al, 2a-hydroxy-
333 ent-Labda-8(17),13E-dien-15-al, 2-oxo-
334 ent-Labda-8(17),13Z-dien-15-al, 2-oxo-
335 ent-Labda-8(17),13E-dien-15-oic acid [E-Copalic acid]
336 ent-Labda-8(17),13Z-dien-15-oic acid [Z-Copa1ic acid]
337 ent-Labda-8(17),13Z-dien-15-oic acid, 3a-hydroxy-
Table I. Compound Numbers and Names 29
TABLE 1. (contd.)
Compound:
No. Name
338 ent-Labda-8(17),13Z-dien-15-oic acid, 3a,7a-dihydroxy-
339 ent-Labda-13Z-en-15-oic acid, 3a-hydroxy-17-oxo-8~-H-
340 ent-Labda-13Z-en-15-oic acid, 3a-hydroxy-17-oxo-8a-H-

341 ent-Labda-13-en-15-oic acid, 3,17-dioxo-8~-H-
342 ent-Labda-13Z-en-15-oic acid, 3,17-dioxo-8a-H-

343 ent-Labda-13Z-en-15-oic acid, 3a,8a-dihydroxy-17-oxo-8~-H
[Published name, "3a,9~-dihydroxy-17-oxo-8~-H-ent-labda-13Z

en-oic acid", was inconsistent with the structure and
published data.]
344 ent-Labda-13Z-en-15,17-dioic acid, 8~-H-
345 ent-Labda-13E-en-15,17-dioic acid, 3~-H-
346 ent-Labda-13Z-en-15-oic acid, 3-oxo-8,17-epoxy-

347 ent-Labda-8(17),13-dien-15-0-bernsteinoate, 8,17-dihydro-8~,
l7-epoxy-
348 ent-Labda-13(14)E-en-15-ol, 8-hydroxy-
349 ent-Labda-13(14)E-en-15-al, 8-hydroxy-
350 ent-Labda-13(14)Z-en-15-al, 8-hydroxy-
351 ent-Labda-7,8,13,14(Z)-diene, 6~,15-dihydroxy-
352 ent-Labda-7,8,13,14(Z)-dien-6-one, l5-hydroxy-

353 ent-Labda-7,13-diene, 3a,15-diacetoxy-ll-hydroxy-
354 ent-Labda-7,13E-dien-15-oic acid

355 ent-Labda-7,13-dien-15-oic acid, 2~-angeloyloxy
[Dendroidinic acid]
356 ent-Labda-6,8(17)-dien-15-oic acid
357 ent-Labda-8(17)-ene, 2a,15-dihydroxy-
358 Eperuic acid, 2a-iso-valeroyloxy-
[e-13 orientivity conflicts with earlier assigned

stereochemistry for this center in eperuic acid.]
857 ent-Labda-8(17)-en-15-oic acid, 2a-hydroxy-

858 ent-Labda-8(17)-en-15-oic acid, 2a-angeloyloxy-
859 ent-Labda-8(17)-en-15-oic acid, 2a-tigloyloxy-
860 ent-Labda-8(17)-en-15-oic acid, 2a-[2-methylbutyryloxy]-
TABLE 1. (contd.)
Compound:
No. Name
861 ent-Labda-8(17)-en-15-oic acid, 2-oxo-
862 ent-Labdan-15-oic acid, 2a-angeloyloxy-8~,17-epoxy-
863 ent-Labdan-15-oic acid, 2a-[2-methylbutyryloxy]-8~,17-epoxy-
359 ent-Labda-8(17)-en-15-o1, 2-oxo-

360 Haplopappus pectinatus ent-labdane 16
361 ent-Labda-7-en-15-oic acid, 2~-angeloyloxy
[13,14-Dihydrodendroidinic acid]
362 ent-Labda-7(8),13E-diene, 15,16,17-trihydroxy-
363 ent-Labda-6,13-diene, 15,16-diacetoxy-
364 ent-Labda-6,13-diene, 15,16,17-triacetoxy-
365 ent-Labda-6,8(17),13-trien-15-oic acid, 16-hydroxy-
366 ent-Labda-7,13E-dien-15-oic acid, 16-hydroxy
367 ent-Labda-7,13E-dien-15-oic acid, 16, 17-dihydroxy-
368 ent-Labda-7,13Z-dien-15-oic acid, 12-hydroxy-16-oxo-
369 ent-Labda-7,13E-dien-15-oic acid, 16-hydroxy-17-oxo-
370 ent-Labda-7,13E-dien-15-oic acid, 17-hydroxy-16-acetoxy-
371 ent-Labda-7,13-dien-15-oic acid, 16-acetoxy-17-oxo-
372 ent-Labda-7,13E-dien-15-oic acid,
16-acetoxy-6a-hydroxy-17-oxo-
16-acetoxy-6~-hydroxy-17-oxo-
374 ent-Labda-7,13Z-dien-15-oic acid, 16-acetoxy-6-oxo-

375 ent-Labda-7,13Z-dien-15-oic acid, 6,16-dioxo-
376 ent-Labda-7,13E-dien-15-oic acid, 16-hydroxy-6-oxo-
377 ent-Labda-7,13E-dien-15-oic acid, 16-acetoxy-6-oxo-
378 ent-Labda-7,13E-dien-15-oic acid, 16-methoxy-6-oxo-
379 ent-Labda-6,13E-dien-15-oic acid, 8a,16-dihydroxy-
380 ent-Labda-6,13E-dien-15-oic acid, 16-acetoxy-17-oxo-
381 ent-Labda-6,13E-dien-15,17-dioic acid, 16-acetoxy-
382 ent-Labda-8(17),13-diene, 7~,15,16-trihydroxy-
383 ent-Labda-8(17)-en-15-oic acid, 16-oxo-

TABLE 1. (contd.)
Compound:
No. Name
384 ent-Labda-6,8(17),13-trien-15-oic acid lactone, 16-hydroxy-
385 ent-Labda-8(17),13-dien-15-oic acid lactone,
16, 19-dihydroxy-
386 ent-Labda-7,13-dien-15-oic acid lactone, 16-hydroxy-
387 ent-Labda-7,13-dien-15-oic acid lactone, 12, 16-dihydroxy-
388 ent-Labda-7,13-dien-15-oic acid lactone, 16, 16a-dihydroxy-
389 ent-Labda-7,13-dien-15-oic acid lactone, 16,16~-dihydroxy-
390 ent-Labda-7,13-dien-15-oic acid lactone,

16, 12, 16-trihydroxy-
391 ent-Labda-7,13-dien-15-oic acid lactone, 16,12,
16a-trihydroxy-
16~-trihydroxy-
393 ent-Labda-7,13-dien-15-oic acid lactone, 16-hydroxy-6-oxo-

394 ent-Labda-7,13-dien-1S-oic acid lactone,
16,16-dihydroxy-6-oxo-
395 ent-Labda-7,13-dien-15-oic acid lactone, 16,
16a-dihydroxy-17-oxo- (Acritolongifo1ide AJ
396 ent-Labda-7,13-dien-15-oic acid lactone, 16,
16~-dihydroxy-17-oxo- (Acrito1ongifolide BJ
397 ent-Labda-8(17),13(14)-dien-16-oic acid lactone, 7~,
15-dihydroxy-
843 Nivenolide
398 ent-Labda-7,13-dien-16-oic acid lactone, 15-hydroxy-
399 ent-Labda-7,13-dien-16-oic acid lactone,
1S,12,lS~-trihydroxy-

15a-trihydroxy-
401 Polyalthine, 7~-hydroxy- (AustrochapatolJ
402 Austrochaparol acetate
403 Daniellol
404 Psiadiol
839 Daniellic acid
840 Daniellic acid, 3a-hydroxy-
841 Daniellol, 18-hydroxy-
TABLE 1. (contd.)
Compound:
No. Name
842 Daniellol, 3a,l8-dihydroxy-19-deoxy-
974 ent-Labda-8(17)-ene, 3a-angeloyloxy-18-hydroxy-13-furyl-
975 ent-Labda-8(17)-ene, 18-angeloyloxy-3a-hydroxy-13-furyl-
830 Polyalthic acid
831 Polyalthic acid, 3a-hydroxy-
832 Polyalthic acid, 3a-angeloyloxy-
833 Polyalthic acid, 3a-[2-methylbutyryloxy]-
834 Polyalthic acid, 3a-isobutyryloxy-
835 Polyalthic acid, 19-hydroxy-
836 Polyalthic acid, 8a,17-epoxy-8,l7-dihydro-
837 Polyalthic acid, 8~,17-epoxy-8,17-dihydro-
838 Polyalthic acid, l7-oxo-8~,17-dihydro-
405 Conyzic acid

406 Austrofolin-12-ol, 12-desoxo-
407 Austrofolin
408 Austrochaparo1 acetate, 18-hydroxy-
409 Austrochaparol acetate, 19-acetoxy-
410 Austrochaparol, 19-oxo-
411 Austrochaparol acetate, 18-oxo-
412 Austrofolin, 3a-hydroxy-
413 Austrofo1in, 3a,12-dihydroxy-12-desoxo-
414 Polyalthine, 17-hydroxy-iso-
415 ent-Labda-7,13(16),14-trien-15,16-epoxy-18-oic acid,
5f),9f)H,10a-
416 ent-Labda-13(16),14-diene, 3a-angeloyloxy-8-hydroxy-15,
l6-epoxy-
417 Austrofolin-15a-ol, 15,16-dihydro-
418 Austrofolin-15f)-ol, 15,16-dihydro-
421 Pumi1oxide, 6f)-hydroxy-
[Published structure indicated a C-7~-hydroxyl group, but

name and data contradicted structure.]
TABLE 1. (contd.)
Compound:
No. Name
422 ent-Biformene
423 ent-Biformene, 18-oxo-
424 Ozic acid, cis-
425 Ozic acid, 12,13E-
[ent-Labda-8(17),12E,14-trien-18-oic acid]
426 Ozic acid, 2a-hydroxy-12,13Z-
427 Ozic acid, 2-oxo-12,13Z-
428 Austroinulin
429 Austroinulin, 6-0-acetyl- [Stevinsol]
808 Austroinulin, 6-angelyl-7-acetyl-
430 ent-Biformene, 12,13E-
431 ent-Labda-8(17),12E,14-triene, 19-hydroxy-
432 ent-Labda-8(17),12E,14-triene, 3a,19-dihydroxy-
433 ent-Labda-8(17),12E,14-triene, 18-hydroxy-
434 ent-Labda--8(17),12E,14-triene, 18,19-dihydroxy-
435 Ozic acid, l~-acetoxy-trans- [l~-acetoxy-ent-Labda-8(17),
12E,14-trien-19-oic acid]
[Published structure contained a C-la-oriented acetate,
while the name indicated that the acetate was ~-oriented.
Although the compound was named as an ozic acid derivative,
the published structure contained an a-oriented carboxyl
function rather than the ~-oriented carboxyl group typical
of ozic acid.]
436 ent-Abienol, 3~-hydroxy-
809 ent-Abienol, 6~,7a-dihydroxy-
810 ent-Abienol, 6~-acetoxy-7a-hydroxy-
811 ent-Abienol, 6~-angeloyloxy-7a-acetoxy-
437 ent-Labda-8(17),14-dien-18-oic acid, 12a,13aZ-epoxy-

438 ent-Labda-8(17),14-dien-18-oic acid, 12~,13~Z-epoxy-
439 ent-Labda-8(17),14-dien-18-oic acid, 12a,13aE-epoxy-

440 ent-Labda-8(17),14-dien-18-oic acid, 12~,13~E-epoxy-[12,
13-Dehydro-12,13a-epoxy-ozic acid]
441 ent-Labda-13(16),14-diene, 8a-hydroxy-
442 ent-Manoo1
TABLE 1. (contd.)
Compound:
No. Name
443 ent-Manool, 2~-hydroxy-
444 ent-Manool, 2a-hydroxy-

445 ent-Manool, 2~-succinyloxy-
446 ent-Manool, 2-oxo-

447 ent-Labda-7,14-diene, 13-hydroxy-
448 ent-Labda-7,14-diene, 3,13-dihydroxy-
449 ent-Labda-7,14-diene, 13-hydroxy-3-oxo-
450 ent-Sclareol, 8-epi-
460 ent-Labda-13-Z-en-15-oic acid, 6,16-dioxo-8,12-oxido-
461 Erigerol [1,6~-dihydroxy-7,8~-epoxydihydrogrendelyl ester
of 3,3-dimethylacrylic acid)
1012 ent-Labda-7(8),13E-diene, 15,18-diacetoxy-2~-hydroxy
[or enantiomer)
1013 ent-Labda-7(8),13E-diene, 18-acetoxy-2~,15-dihydroxy
[or enantiomer)
1014 ent-Labda-8(17),13E-diene,3a-acetoxy-15-hydroxy-18-
tigloyloxy- [or enantiomer)
1015 Abieno1, 18-hydroxy-
1016 ent-Labd-8,14-diene, 13,18-dihydroxy-7-oxo-ent-
1017 ent-Labd-14-ene, 18-hydroxy-7-oxo-9~,13~-epoxy-
1018 ent-Labd-14-ene, 7,18-dioxo-9~,13~-epoxy-
1019 ent-Labd-14-en-18-oic acid, 7-oxo-9~,13~-epoxy-
1037 ent-Labda-8(17),13(16),14-triene,
18-hydroxy-3a-angeloyloxy-15,16-epoxy-
1038 ent-Labda-8(17),13(16),14-triene,2~,18-dihydroxy-
3a-angeloyloxy-15,16-epoxy-
1039 ent-Labda-8(17),13Z-diene, 2~,15,16,
18-tetrahydroxy-3a-angeloyloxy-
1040 ent-Labda-8(17),13E-dien-15-oic acid, [E-Copalic acid)
[Structure is the same as 335.)
1041 ent-Labda-8(17),13E-dien-15-oic acid, 18-hydroxy-
1042 ent-Labda-7(8),13E-dien-15-oic acid, 6~-hydroxy-18-oxo-
1043 ent-Labda-7(8),13E-dien-15,
18-dioic acid, 6~-isovaleryloxy-
TABLE 1. (contd.)
Compound:
No. Name
1044 ent-Labda-13E-en-15-oic acid, 5~,8~-peroxy-
1045 ent-Labda-7,13E-dien-15-oic acid, 6~,18-dihdroxy-
1046 ent-Labda-7-en-15-oic acid, 17-hydroxy-

1047 ent-Labda-7-en-15-oic acid, 17-acetoxy-
1048 ent-Labda-7-en-15-oic acid, 17-oxo-
1049 ent-Labda-7-en-15-oic acid, 2a,17-dihydroxy-
1050 ent-Labda-7-en-15-oic acid, 2a-hydroxy-17-acetoxy-
1051 ent-Labda-7-en-15-oic acid, 2a-hydroxy-17-oxo-
1052 ent-Labda-7-en-15,17-dioic acid
1053 ent-Labda-7-en-15-oic acid, 19-hydroxy-17-acetoxy-
1164 ent-Labd-8(17),13E-dien-15,18-dioic acid [Guamaic acid]
1165 ent-Labd-7,13E-dien-2-0-~-fucopyranoside, 3a-ange1oyloxy-
2~,15-dihydroxy-
1166 ent-Labd-7,13E-dien-2-0-~-[fucopyranoside-4'-O-acetate],
3a-angeloyloxy-2~,15-dihydroxy-
1167 ent-Labd-7,13E-dien-2-0-~-[fucopyranoside-3'-O-acetate], 3a-

angeloyloxy-2~,15-dihydroxy-
1168 ent-Labd-7,13E-dien-2-0-~-[fucopyranoside-4'-O-acetate],
3a-angeloyloxy-2~,15,16-trihydroxy-
1169 ent-Labd-7,13(16)-dien-2-0-~-[fucopyranoside-4'-O-acetate],
3a-angeloyloxy-2~,14,15-trihydroxy-
1170 ent-Labd-7,13E-dien-2-0-[rhamnopyranoside-4'-O-acetate],
1171 ent-Labd-7,13E-dien-2-o-~-xylopyranoside,
1172 ent-Labd-13E-ene-8-0-~-xylopyranoside, 8~,15-dihydroxy-
1173 ent-Labd-8(17)-en-19-oic acid, 15-hydroxy-

1174 ent-Labd-13E-ene, 2~,8~,15-trihydroxy-

1176 Haplopappus pectinatus ~-labdane 14
1179 ent-Labd-7-en-15-oic acid, 2-hydroxy-17-methoxy-
TABLE 1. (contd.)
Compound:
No. Name
1180 ent-Labd-7,13(14)-diene-1s-oic acid, 16-hydroxy-17-methoxy-
1181 ent-Labd-8(17),13-dien-1s,16-olide, 2~,18-dihydroxy-
1182 ent-Labd-8(17),13-dien-1s,16-olide, 3a-angeloyloxy-18-

hydroxy-
1183 ent-Labd-8(17),13-dien-1s,16-olide, 3a-angeloyloxy-18~
glucopyranosyloxy-
1184 ent-Labd-8(17),13-dien-1s,16-olide, 3a-angeloyloxy-2~,18~
dihydroxy-
1185 ent-Labd-8(17),12E,14-triene, 18,19-diacetoxy-
1186 ent-Biformene, 3a,14,ls-trihydroxy-12E,14,ls-dihydro-
1188 ent-Labda-7,13(16),14-trien-2~,3a-diol, ls,16-epoxy-
1189 ent-Labd-8(17),13E-dien-1s-oic acid, 3a,18-dihydroxy-
1190 ent-Labd-8(17),13E-dien-1s-oic acid, 3a-angeloyloxy-18-
hydroxy-
1191 ent-Labd-8(17),13Z-diene, 2~,ls,16,18-tetrahydroxy-3a
ange1oyloxy-
1192 ent-Labd-7,13-dien-2~,1s-diol, 3a-angeloyloxy-
1193 ent-Labd-7,13E-diene, 2~,3~,15-trihydroxy-
1194 Gutierrezia spathu1ata ent-labdane 4

1195 Gutierrezia spathulata ent-labdane 5
1196 ent-Cativic acid, 2~,3~-dihydroxy-
1197 ent-Labd-7-ene, 2~,3~,ls-trihydroxy-
39. ent-Labdane-19,6-Lactone
462 Hartwrightia acid
40. ent-Labdane-8,13-Epoxide-ls,16-Hemiacetal
463 Schkuhriadiol, cyclo-
464 Schkuhriadiol-16-0-acetate, cyclo-
97. ~-Labdane Dimer
419 Acritopappus lactone A

TABLE 1. (contd.)
Compound:
No. Name
420 Acritipappus lactone B
98. ent-Manoyl Oxide, 13-Epi-

451 ent-Manoyl oxide, 13-epi- [ent-8,13~-Epoxy-14-labdene)
452 ent-Manoyl oxide, 3a-hydroxy-

453 ent-Manoyl oxide, 3-oxo-13-epi- [ent-8,
13~-epoxy-14-labden-3-one)
454 ent-Manoyl oxide, 2-oxo-13-epi-

455 ent-Manoyl oxide, 19-hydroxy-13-epi-
456 ent-Manoyl oxide, 2-oxo-19-hydroxy-13-epi-
457 Schkuhrianol acetate [16-acetoxy-14,15-epoxy-14,
15-dihydro-13-epi-ent-Manoyl oxide)
1198 ent-Manoyl oxide, 3a-acetoxy-
1199 ent-Manoyl oxide, 19-cinnamoyloxy-3a-hydroxy-
99. ent-Manoyl OXide

458 ent-Manoyl oxide
459 ent-Manoyl oxide, 3~-hydroxy-
[This structure is apparently identical to a compound from

coespeletia lutescens named 3~-Hydroxy-13-epi-ent-manoyl
oxide for which the published structure did not indicate a
13-epi-orientation.)
41. ent-Labdane, 17-Nor-

16-acetoxy-8~-formyl-8-desmethyl-

16-acetoxy-8-oxo-8-desmethyl-
467 Ayapanone acid, 3a-hydroxy-
468 Ayapanone acid, 3-oxo-
1201 ent-Labda-13Z-en-15-oic acid, 8-oxo-8-desmethyl-
1202 ent-Labda-13Z-en-15-oic acid, 3,8-dioxo-
TABLE 1. (contd.)
Compound:
No. Name
469 ent-Labda-8(17),12E-diene, 14-oxo-nor-15-
43. ent-Labdane, 14,15-Bis-Nor-

470 ent-Labda-8(17)-ene, 13-oxo-bis-nor-14,15-
1203 ent-Labd-7-en-2-0-[fucopyranoside-4'-O-acetate],
14,15-nor-
44. ent-Labdane, 13,14,15,16-Tetra-Nor-

471 ent-Labda-7-en-aldehyde, nor- [Tetra-nor-13,14,15,
16-12-oxo-ent-labda-7-ene]
472 Acritoconfertic acid [Tetra-nor-13,14,15,
16-17-hydroxy-ent-labda-7-en-12-oic acid]
45. ent-Labdane, 7,8-Seco-

473 Athrixic acid, seco-

828 ent-Labdane trio1 la, nor-18-
829 ent-Labdane trio1 2a, nor-18-
1205 Austroeupatorione, 12-desoxo-
1206 Austroeupatorione, 12-desoxo-2-desacetyl-
1207 Austroeupatorione
95. ent-Friedolabdane
1059 ent-Labda-5,13E-dien-15-oio acid,
18-hydroxy-10-desmenthyl-9a-methyl-8~(H)-
1208 [= 1059)
1209 ent-Friedolabd-1(10),13E-dien-15-o1, 2-oxo-
1210 ent-Friedo1abd-1(10),13E-diene, 2a,15-dihydroxy-
1211 Friedo1abdaturbinic acid
TABLE 1. (contd.)
Compound:
No. Name
1212 Chiliolide, 3a,5a-dihydroxy-

1213 Chiliolide, 3a-hydroxy-5,6-dehydro-
1214 Chi1iolide, 3a-hydroxy-5~,10~-epoxy-
102. ~-Friedolabdane, 3,4-Seco-

1215 Chilio1ide aldehyde, seco-
1216 Chilio1ide acid, seco-
1217 Chi1io1ide, 19-hydroxy-seco-
1218 Chi1io1ide acid methyl ester, 19-hydroxy-
1219 Chi1io1ide lactone, seco-
1220 Chiliotrin, seco-
103. ent-Friedolabdane, Rearranged 3,4-Seco-

1221 Chilio1ide lactone, iso-
46. trans-ent-Clerodane
236 Bedfordia diterpene alcohol
248 So1idago-18-oic acid, 8-epi-1,2-dehydro- [Reported as

5~,10a-trans-c1erodane]
249 Solidago-18-oic acid, 8-epi- [Reported as 5~,10a-trans-

clerodane; probably (-)-hardwickiic acid] ------
250 Solidago-18-oic acid, 1,2-dehydro- [Reported as 5~,10a
~-c1erodane with C-8~-methy1;probab1y = 248]
251 Solidago-18-oate, methyl 8-epi-1,2-dehydro- [Nidoreseda
acid methyl ester; Reported as 5~,10a-~- c1erodane]
245 Solidago-18-oic acid [Reported as 5~,10a-trans-clerodane
with C-8~-methy1; probably the same as 249-)----
475 Ko1aveno1
476 Ko1aveno1, 17-hydroxy-13E-
477 Kolavenol acetate, 2a-hydroxy-3~,4~-epoxy-3,4-dihydro-
478 Ko1avenol acetate, 2a,l6-dihydroxy-3~,4~-epoxy-3,4-dihydro-

TABLE 1. (contd.)
Compound:
No. Name
1010 Kolavenol arachidate, 17-hydroxy-13E-

1011 Kolavenol behenate, 17-hydroxy-13E-
479 Kolavelool (Kolavenool]
480 Kolavelool, 6~-angeloyloxy- (6~-Angeloyloxy-kolavenool]
481 Kolavenol, 17-hydroxy-13,14-dihydro-

482 Kolavenol arachidate, 17-hydroxy-13,14-dihydro-
483 Kolavenol behenate, 17-hydroxy-13,14-dihydro-
484 Kolavenol, 18-succinyloxy-13,14-dihydro-
485 Kolavenol, 2a-hydroxy-3a,4a-epoxy-13,14-dihydro-
486 Kolavenol, 17-oxo-13,14-dihydro-
487 Gochnatol-17-0-acetate
488 Kolav-3-en-15-o1, 6a,18-dihydroxy-17-acetoxy-
489 Kolav-3-en-15-o1, 6a,18-dihydroxy-17-phenylacetoxy-
490 Ko1av-3-en-15-o1, 6a-hydroxy-17-phenylacetoxy-18-oxo-
491 Kolav-3-en-15-o1, 6a-hydroxy-17-acetoxy-18-oxo-
492 Kolaven-15-al, 17-hydroxy-13,14-dihydro-
493 Kolavenoic acid, 13,14Z-
494 Kolavenoic acid, 2~-acetoxy-13,14Z-
495 Ko1avenoic acid (13,14E-Kolavenoic acid]

496 Kolavenoic acid, 6-acetoxy- (6~-Acetoxy-13 ,
14E-kolavenoic acid]
497 Kolavenoic acid, 6-angeloyloxy- [6~-Angeloyloxy-13,
498 Kolavenic acid, 6-angeloyloxy- [6a-Angeloyloxy-13,
499 Kolavenic acid, 6-tigloyloxy- (6a-Tigloyloxy-13,
500 Solidagonic acid (7a-Acetoxy-13,
962 Tucumanoic acid
501 Kolavenoic acid, 6a,18-dihydroxy-17-acetoxy-
502 Kolavenoic acid, 6a,18-dihydroxy-17-phenylacetoxy-
TABLE 1. (contd.)
Compound:
No. Name
503 Kolav-3-en-15-oic acid, 13,14-dihydro-
504 Kolav-3-en-15-oic acid, 18-acetoxy-
961 Kolavenic acid, 2-oxo-
505 Haplociliatic acid
506 Kolavan-2-on-15-oic acid, 3~,4~-epoxy-
507 Kolav-3,13(16),14-triene, 15,16-epoxy-

508 Bacchalineol malonate
509 Bacchotricuneatin D
846 Kingidiol [Barticulidiol J
510 Barticulidiol, 18-acetoxy-19-malonyloxy-
967 Cleroda-3,13(16),14-trien-15,16-oxide, 17-oxo-
511 Hardwickiic acid, (-)-
[= 517J
953 Hardwickiic acid, 12a-[2-methylbutyryloxy}-(-)-

512 ent-cleroda-1,3,13(16),14-tetraen-18-oic acid, 15,
16-epoxy-
911 Hautriwaic acid, 19-0-acetyl-1,2-dehydro-
513 ent-Kolav-3,13(16),14-trien-18-oic acid, 2~-hydroxy-15,
16-epoxy-
514 Imbricato1-isovalerate, 3-hydroxy-
515 Imbricatol-a-methylbutyrate, 3-hydroxy-
516 Imbricatol-angelate, 3-hydroxy-
518 Kolav-3,13(16),14-trien-18-oic acid, 15,
l6-epoxy-19-hydroxy-ent- [Hautriwaic acid}
519 Ko1av-3,13(16),14-trien-18-oic acid, 15,16-epoxy-2a,
19-dihydroxy-ent-
900 Hautriwaic acid, 19-acetyl-
901 Hautriwaic acid, 10-0-methyl
902 Hautriwaic acid, 19-0-angelyl-
903 Hautriwaic acid, 19-0-isovaleryl-
904 Hautriwaic acid, 19-oxo-
524 ent-Ko1av-3,13(16),14-trien-20-oic acid, 15,
16-epoxy- [Junceic acidJ
TABLE 1. (contd.)
Compound:
No. Name
520 Hautriwaic acid lactone
950 Hautriwaic acid-l9-lactone, 12a-hydroxy-
951 Hautriwaic acid-19-lactone, 7a,12a-dihydroxy-
521 Bacchofertin
522 Gochnatoic acid-17-0-phenylacetate
523 Hardwickiic acid lactone, 7-oxo-6a-hydroxy
525 Conycephaloide
526 conycephaloide, 7-hydroxy-17-oxo-7,8-dehydro-8,17-dihydro-
527 Bacchotricuneatin A
528 Bacchotricuneatin C
969 Conycephaloide, 12-epi-
970 Conycephaloide, 12-epi-8~,17-dihydro-
971 Salviarin, 6a-angeloyloxy-1-oxo-2,3-dihydro-

972 Bacchotricuneatin A, 6~-hydroxy-7,8-dehydro-
973 Salviarin
529 Bacchotricuneatin B
968 Bacchotricuneatin B, 2a-angeloyloxy-
530 Bacchotricuneatin B, 7~-angeloyloxy-
531 Bacchotricuneatin, 2a-angeloyloxy-3a-senecioyloxy-3,4~H-
532 Bacchotricuneatin, 2a-senecioyloxy-3a-angeloyloxy-3,4~H-
533 Bacchotricuneatin,2a-angeloyloxy-3a-[2-methylbutyryloxy]-
3,4~H-
534 Kolaven-15-al, 17-hydroxy-13Z-

535 Kolaven-15-al, 17-hydroxy-13E-
536 Symphyoreticulic acid, 13Z-
537 Symphyoreticulic acid, 13E-
865 Kolava-3,13E-dien-15-oic acid, 16-hydroxy-
962 Solidagonic acid
538 Kolavenic acid, 16,18-dihydroxy-
539 Kolavenic acid, 16-acetoxy-18-hydroxy-

TABLE 1. (contd.)
Compound:
No. Name
540 Kolavenic acid, 16-hydroxy-18-oxo-
541 Kolavenic acid, 16-acetoxy-18-oxo-
542 Kolav-3-en-15-oic acid, 16-oxo-
543 Solidagolactone [soldagolactone I; 16-Hydroxy-kolavenic
acid lactone)
544 Kolavenic acid lactone, 2a,16-dihydroxy-
864 Kolava-3,13Z-dien-15-oic acid lactone, 16,16-dihydroxy-
550 Kolavenic acid lactone, 16,18-dihydroxy-
551 Kolavenic-15-acid lactone, 2a,16-dihydroxy-3a,4a-epoxy-
[Revised to cis-norma1-clerodane)
552 Kolavenic-15-acid lactone, 6~-angeloyloxy-16-hydroxy-3a,
4a-epoxy-
[Revised to cis-normal-clerodane)
558 Hardwickiic acid, 15,16H-15-oxo-
[Compound was named as "16-oxo- .•. ", but data and structure
indicate otherwise.)
909 Hautriwaic acid, 16a-acetoxy-19-0-acetyl-15-oxo-15,
16-dihydro-
910 Hautriwaiic acid, 16~-acetoxy-19-0-acetyl-15-oxo-15,
16-dihydro-
559 Kolaven-15,
18-dioic acid dilactone, 7a,16,19-trihydroxy-
560 Olearin
561 Kolaven-15,18-dioic acid dilactone,7-oxo-16,
19-dihydroxy-13,14-dihydro-
562 Kolaven-15,18-dioic acid dilactone, 7a,16,19-trihydroxy-13,
14-dihydro-
563 Kolaven-15,18-dioic acid di1actone, 16, 19-dihydroxy-13,
14-dihydro-
564 Kolaven-15-oic acid lactone, 16-hydroxy-13,
14-dihydro-
565 Kolav-3-en-15-oic acid lactone, 16,16-dihydroxy-
963 Kolaven-15-oic acid lactone,
16-hydroxy-16-methoxy-18-acetoxy-
566 Rugosolide
905 Hautriwaic acid, 15a-hydroxy-16-oxo-15,16-dihydro-
TABLE 1. (contd.)
Compound:
No. Name
906 Hautriwaic acid, 15~-hydroxy-16-oxo-15,16-dihydro-
907 Hautriwaic acid, 14a,15a-epoxy-16-oxo-13,14,15,

16-tetrahydro-
908 Hautriwaic acid, 14~,15~-epoxy-16-oxo-13,14,15,
16-tetrahydro-
567 Kolaven-16-oic acid lactone, 2~,15-dihydroxy-
568 Kolaven-16-oic acid lactone, 15-hydroxy-2-oxo-

569 Ko1av-3-ene, 18-malonyloxy-15-hydroxy-15,16-epoxy-
570 Stephalic acid
1027 Ko1avenic acid, 6a-isobutyryloxy-7~-acetoxy-13-Z-
1028 Kolavenic acid, 6a-angeloyloxy-7~-acetoxy-13Z-
1029 Kolavenic acid, 6a,7~-diacetoxy-13Z-
1030 Kolavenic acid, 6a,7~-dihydroxy-2-oxo-13E-
1031 Kolavenic acid, 6a-isobutyryloxy-7~-angeloyloxy-13,

14-dihydro-
1033 Hautriwaic Acid
[= 518]
1034 Hautriwaic acid, 2~-hydroxy-
1069 Bacchotricuneatin A, 1a-hydroxy-

1070 Hautriwaic acid, 1,2-dehydro-
1071 Junceic acid epoxide
1075 Ko1av-13Z-en-15-al, 3a,4a-epoxy-
1076 Kolav-13(16),14-diene, 3a,4a,15,16-diepoxy-
1077 Kolav-13E-en-15-a1, 3a,4a-epoxy-
1078 Kolav-13Z-en-15-al, 3-oxo-
1079 Kolav-13E-en-15-al, 3-oxo-
1080 Kolav-13-en-15-oic acid lactone, 16-hydroxy-3a,4a-epoxy-
1081 Kolav-13-en-15-oic acid lactone, 16-hydroxy-3-oxo-
1082 Kolav-13-en-15-oic acid lactone, 16,3a,4~-trihydroxy
1222 Bincatriol
1223 Salvicin [19-Carboxy-6a,15-dihydroxy-trans-cleroda-
3,13(14)-dienel
TABLE 1. (contd.)
Compound:
No. Name
1224 Bacchasalicyc1ic acid

1225 Bacchasalicyclic acid-15-0-acetate, 16-hydroxy-
1226 Bacchasalicyclic acid-15-0-[1r-~-xylopyranosidel
1227 Baccharis incarum neoclerodane 1

1228 Kolavenol acetate, 16-hydroxy-2a-acetoxy-3~,4~-epoxy-3,4-
dihydro-
1229 Baccharis rhomboidalis neoclerodane 5
1231 Kingidiol, 19-0-malonyl-
1232 Bacchalineol
1233 Barticulidiol
1234 Salvin [15,16-Epoxy-trans-cleroda-3,13(16),14-trien-19,6~
olide 1
1235 Salvinin [7-Hydroxy-15,16-epoxy-trans-cleroda-3,13(16),14-
trien-19,6~-olidel

1237 Articulin
1238 Articulin acetate
1239 Baccharis grandicapitulata neoclerodane 16
1244 Bacchomagellin A
1245 Bacchomagellin B
1257 Bacchotricuneatin A, la-acetyl-
1258 Bacchotricuneatin A, 7a-hydroxy-
47. Printziane
571 Printzianic acid
TABLE 1. (contd.)
Compound:
No. Name
572 Printzianic acid, iso-
913 Printziaic acid, 5a-hydroxy-5,10-dihydro-
914 Printziaic acid, 5a-methoxy-5,10-dihydro-
915 Printziaic acid, 5a-hydroxy-1,2-dehydro-5,10-dihydro-
916 Printziaic acid lactone, 5a-hydroxy-5,10-dihydro-
76.Conyscabrane
917 Conyscabraic acid, 5,6-dehydroiso-
918 Conyscabraic acid, 5,6-dehydro-
919 Conyscabraic acid, 5a-hydroxyiso-
920 Conyscabraic acid, 5a-hydroxy-
48. ent-Clerodane, 5,10-Seco-

573 Strictic acid
912 Nidoresedaic acid, 19-acetoxyseco-
985 Pulicaria anqustifolia compound 1a
952 Strictic acid, 12a-[2-methylbutyryloxy]-
96. trans-~-Clerodane, 17-Nor-

1061 Bacchascoparone
49. ~-ent-Clerodane, 13,14,15,16-Tetra-Nor-

574 Acritopappusol
575 Acritopappus acid
1032 Kolavenic acid, 6a,7~-dihydroxy-nor-
1093 Hautriwaic acid, 13,14,15,16-tetranor-1,2-dehydro-

TABLE 1. (contd.)
Compound:
No. Name
Undetermined
237 Bedfordia diterpene alcohol, iso- [Clerodane of unknown
absolute stereochemistry]
50. cis-ent-Clerodane
578 Cleroda-3,13(16),14-triene, 15,16-epoxy-cis-
579 Cleroda-3,13(16),14-triene, 18-hydroxy-15,16-epoxy-cis-
580 Cleroda-3,13(16),14-triene, 18-acetoxy-15,16-epoxy-cis-
576 Haplopappic acid
577 Haplopappate, monomethyl-
581 Cleroda-3,13(16),14-triene, 6a,18-dihydroxy-15,16-epoxy-cis-
582 Cleroda-3,13(16),14-triene, 6a-hydroxy-18-acetoxy-15,
16-epoxy-cis-
583 Cleroda-3,13(16),14-trien-18,6a-olide, 15,16-epoxy-cis-
584 Cleroda-3-en-15,16,18,6a-diolide, cis-
585 Cleroda-3-en-15,16,18,6a-diolide, 2~-hydroxy-cis-
1055 Cleroda-3,13E-dien-15-oic acid, '18-acetoxy-cis-

1056 Cleroda-3,13E-dien-15-oic acid, 18-hydroxy-cis-
1057 C1eroda-3-en-15-oic acid, 18-hydroxy-cis-
1058 Cleroda-3-en-15-oic acid, 19-hydroxy-
1246 Chiliomarin
82. Solidagonane
960 Solidagona1 acid
VI. ent-Tricarbocyclics and Derivatives

51. ent-Labdane, Cyclopropyl-
586 Gnapha1ene, 8a,13a-dihydroxy-
77. Gutierreziane
845 Gutierrezia1
TABLE 1. (contd.)
Compound:
No. Name
52. ent-Pimarane
587 Sandaracopimar-15-en-8~-ol [Published structure incorrectly
drawn = Cmpd No. 276)
588 Sandaracopimar-15-en-8~,11a-diol 12~-acetoxy
[Structure incorrectly drawn = C~pd No. 292)
589 Kirenol
590 Pimara-8(14),15-dien-l9-oic acid, ent-
820 Pimara-7,15-dien-19-oic acid, ent-
821 Pimara-8,15-dien-19-oic acid, ent-7-oxo-
823 Pimara-9(11)-en-19-oic acid, ent-12~-acetoxy-
591 Darutigenol
592 Darutigenol-3a-glucoside
593 Pimara-8(14)-en-6~-O-glucoside, 15~,16-dihydroxy
594 Pimara-8(14)-ene, 6~,15~,16-trihydroxy-
595 Pimara-8(14)-ene, 2~,15~,16,19-trihydroxy-
944 Pimara-8(14)-ene, ent-6~,15,16,18-tetrahydroxy-
599 Pimar-9,11(15)-dien-19-o1, (-)-

600 pimar-9,11(15)-dien-19-oic acid, (-)-
1247 ent-8(14),15-Pimaradiene-3~,19-diol
1248 ent-8(14),15-Pimaradiene-3~,18-diol
1249 ent-Pimar-8(9),15-diene, 20-hydroxy-7-oxo-

1250 ent-Pimara-9(11),15-dien-19-o1
1251 ent-Pimara-9(11),15-diene, 18-hydroxy-
1252 ent-Pimar-9(11),15-diene malonate, 18-hydroxy-
1253 ent-Pimar-9(11),15-diene malonate, 19-hydroxy-
1254 ent-Pimar-9(11),15-diene, 3a,19-dihydroxy-
53. ~-Pimarane-8,15-Tetrahydrofuran
596 Pimara-3~,12a,16-triol C-15-epimer 9a, ent-8,15-epoxy-

597 Pimara-3~,12a,16-triol C-15 epimer lOa, ent-8,15-epoxy-
TABLE 1. (contd.)
Compound:
No. Name
824 Pimar-9(11)-en-19-oic acid, ent-8(R),
15(S)-epoxy-12a-acetoxy-
598 Pimara-12a,16-diol, ent-8,15R-epoxy-3-oxo-
54. Cleistanthane (Cleistanthol)

601 Cleistanth-12-en-1l-one, 15,16-epoxy-
602 Cleistanth-12-en-17-al, l5,16-epoxy-ll-oxo-
603 Cleistanth-12-en-l1-one, 17-acetoxy-15,16-epoxy-
604 Cleistanth-12-en-l1-one, 3a-angeloyloxy-15,16-epoxy-
605 Cleistanth-12-en-ll-one, 17-acetoxy-14~-hydroxy-15,16-epoxy-
606 Cleistanth-12-en-ll-one,
l7-acetoxy-3a-angeloyloxy-15,16-epoxy-
607 Cleistanth-12-en-17-al, 11-oxo-8,9,15,16-diepoxy-
608 Cleistanth-12-en-ll-one, l4~,15~-dihydroxy-16,17-oxido-
85. Cleistanthane, Iso-

609 Cleistanth-12-en-11-one, 17-acetoxy-l5,16-epoxy-iso-
610 Cleistanth-12-en-ll-one, l7-acetoxy-3,4,15,16-diepoxy-iso-
55. ent-Abietane
611 Missourienol A [initially isolated as dehydration product:

3-oxo-abieta-7,13-diene]
612 Missourienol B [initially isolated as dehydration
product:3~-hydroxy-abieta-7,13-dienel
613 Missourienol C [initially isolated as dehydration

product:2~-acetoxy-abieta-7,13-dienel
614 Abieta-7,13-diene
615 Abieta-7,13(14)-diene, 5-acetoxy-
616 Abieta-7,13(14)-dien-l8-oic acid
1054 Abieta-7,13-diene, 19-succinyloxy-
56. Acritoconfertane
617 Acritoconfert-7-en-15-oic acid, 16-acetoxy-17-hydroxy-
TABLE 1. (contd.)
Compound:
No. Name
57. Acritoconfertane-Acetal
1100 Acritoconfertic acid, 8,16,16,17-bisoxido-
83. Erythroxane
976 Erythroxa-3,15-dien-18-oic acid
VII. !m!:-Tetracarbocyclics and Derivatives

58. ent-Kaurane
618 Kaur-16-ene, ent-
619 Kaur-16-ene, 19-hydroxy-ent-
997 Kaurano1, ent- [(-)-kaurano1]
620 Kaur-16-ene, 19-acetoxy-ent-
621 Kaurene, 19-formyloxymethylenoxy-ent-
622 Kaurene, 19-[p-hydroxyhydrocinnamoyloxy]-ent-
623 Kaur-16-en-3a,19-diol, (-)-
626 Kaur-16-ene, 18-acetoxy-ent-
624 Kaur-16-ene, 19-oxo-ent-
625 Kauren-19-oic acid, ent-
926 Kauren-18-oic acid, ent-
[Although referred to as kaurenic acid, the published
structure of this compound from Melampodium perfoliatum
contained a C-4~-oriented carboxyl group.]
939 Kaurenic acid, 18-angeloyloxy-
[Although referred to as a kaurenic acid derivative, the
published structure of this compound from Melampodium
perfoliatum contained a C-4~-oriented carboxyl group and a
C-4a-oriented ester function.]
627 Kaur-16-en-19-oic acid glycol ester, ent-
628 Kaur-16-en-19-oic acid, 3a-hydroxy-ent-
629 Kaur-16-en-19-oic acid, 3a-acetoxy-ent-
630 Kaur-16-en-19-oic acid, 3a-angeloyloxy-ent-
631 Kaur-16-en-19-oic acid, 3a-tigloyloxy-ent-
632 Kaur-16-en-19-oic acid, 3a-cinnamoyloxy-ent-
TABLE 1. (contd.)
Compound:
No. Name
633 Kaur-16-en-19-oic acid, 3a-senecioyloxy-ent-
634 Kaur-16-en-19-oic acid, 3a-isovaleryloxy-ent-
635 Kaur-16-en-18-al, ent-
636 Kaur-16-en-19-oic acid, 9~,13~-dihydroxy-15a-
angeloyloxy-ent-
637 Kaur-16-en-19-oic acid, 11~,15a-dihydroxy-ent-
638 Kaurane, 18-hydroxy-16a, 17-epoxy-ent-

1000 Kaur-16-en-19-oic acid; 7~-hydroxy-(-)-
639 stenolobin
640 Kaur-16-en-19-oic acid, 11~-acetoxy-ent-

1108 [= 642)
643 Kaur-16-en-19-oic acid, 18-angeloyloxy-ent-
644 Kaur-16-en-19-oic acid, 18-senecioyloxy-ent-
645 Kaur-16-en-19-oic acid, 18-isovaleryloxy-ent-
646 Grandifloric acid (15a-hydroxy-ent-kaur-16-en-19-oic acid)
647 Kaur-16-en-19-oic acid, 15~-hydroxy-ent-

649 Kaur-16-en-19-oic acid, 15a-angeloyloxy-ent-
1007 Stenolobin, 15a-angeloyloxy-
[methyl-15a-angeloy1oxy-ent-kaur-16-en-19-oate)
650 Kaur-16-en-19-oic acid, 15a-tigloyloxy-ent-
651 Kaur-16-en-19-oic acid, 15a-senecioyloxy-ent-
652 Kaur-16-en-19-oic acid, 15a-isovaleryloxy-ent-
653 Kaur-16-en-19-oic acid, 15a-[2-methylacryloyloxy)-ent-
654 Kaur-16-en-19-oic acid, 15a-isobutyroyloxy-ent-
655 Kaur-16-en-19-oic acid, 15a-cinnamoyloxy-ent-
[cinnamoyloxygrandifloric acid)
656 Kauren-16-en-19-oic acid, 15a-[2,
3-epoxy-2-methylbutyloxy)-ent-
657 Kaur-16-en-19-oic acid, 15a-benzoyloxy-ent-
TABLE 1. (contd.)
Compound:
No. Name
818 Kauren-16-en-19-oic acid,15a-[2',
3'-dihydroxy-2-methylbutyryloxy]-ent-
892 Kaur-16-en-19-oic acid, 15a[2'-methylbutyry1oxy]-ent-
658 Kaur-16-en-19-oic acid, 15~-angeloyloxy-ent-
659 Kaur-16-en-19-oic acid, 15~-tigloyloxy-ent-
660 Kaur-16-en-19-oic acid, 15~-senecioyloxy-ent-
661 Kaur-16-en-19-oate, methyl-15a-hydroxy-ent- [grandifloric

acid methylesterj
662 Kaur-16-en-19-oic acid, 3a-angeloyloxy-9~-hydroxy-ent-
663 Kaur-16-en-19-oic acid, 3a-cinnamoyloxy-9~-hydroxy-ent-
664 Kaur-16-en-19-oic acid, 9~,15a-dihydroxy-ent

[grandifloric acid, 9~-hydroxy]
665 Kaur-16-en-19-oic acid, 9~-hydroxy-15a-angeloyloxy-ent-
666 Kaur-16-en-19-oic acid, 9~-hydroxy-15a-tigloyloxy-ent-
667 Kaur-16-en-19-oic acid, 9~-hydroxy-15a-acetoxy-ent-
668 Kaur-16-en-19-oic acid, 9~-hydroxy-15a-senecioyloxy-ent-
669 Kaur-16-en-19-oic acid, 9~-hydroxy-15a-isovaleryloxy-ent-
670 Kaur-16-en-19-oic acid, 9~-hydroxy-15a-cinnamoyloxy-ent-
819 Kaur-16-en-19-oic acid, 9~-hydroxy-

15a-[3'-hydroxy-2'-methylbutyryloxy]-ent-
671 Kaur-16-en-19-oic acid, 11~,15~-dihydroxy-ent-
812 Kaur-16-en-19-oic acid, 17-carbomethoxy-ent-

672 Kaur-16-en-19-oic acid, 11~-hydroxy-15~-acetoxy-ent-
673 Kaur-16-en-19-oic acid, 15~-hydroxy-11-oxo-ent-
674 Kaur-16-en-19-oic acid, 11~-hydroxy-15-oxo-ent-
1260 Kaur-16-en-19-oic acid, 11~,12~,15~-trihydroxy-ent-
675 Kaur-16-en-19-oic acid, 3~,9~-dihydroxy-15a-angeloyloxy-ent-
869 Kaur-16-en-19-oic acid,

9~,11~-dihydroxy-15a-angeloyloxy-ent-
676 Kaur-16-en-19-oic acid, 3~,

9~-dihydroxy-15a-senecioyloxy-ent-
677 Kaur-16-en-19-oic acid, 3~,9~-dihydroxy-15a-tigloyloxy-ent-

TABLE 1. (contd.)
Compound:
No. Name
945 Doronicoside D
678 Carboxyatractyloside
679 Wedeloside
680 Wedeloside, L-rhamnopyranosyl-
681 Atractyloside
895 Paniculoside I
896 Paniculoside II
897 Paniculoside III
898 Paniculoside IV
899 Paniculoside V
682 Steviolbioside
683 Stevioside
684 Rebaudioside B
685 Rebaudioside A
686 Dulcoside A
687 Dulcoside B
688 Rebaudioside D
689 Rebaudioside E
690 Kaur-9(11),16-dien-19-oic acid, ent-
691 Kaur-9(11),16-dien-19-oic acid, 2[3-hydroxy-ent-
694 Kaur-9(11),16-dien-19-oic acid, 12[3-hydroxy-
998 Kaur-9(11),16-dien-19-oic acid, 12[3-ethoxy-ent-
695 Kaur-9(11),16-dien-19-oic acid, 12-oxo-ent-
696 Kaur-9(11),16-dien-19-oic acid, 15a-hydroxy-ent-
697 Kaur-15-ene, 17-hydroxy-ent- [17-hydroxy-isokaurene]
698 Kaur-15-ene, 17,19-dihydroxy-ent-
699 Kaur-15-ene, 17-hydroxy-19-[p-hydroxy-hydrocinnamoyloxy]-
[17-hydroxy-19-[p-hydroxy-hydrocinnamoyloxy)-isokaurene)
TABLE 1. (contd.)
Compound:
No. Name
946 Kaur-15-en-19-al, (-)-
700 Kaur-15-en-19-oic acid, ent-
701 Kaur-15-en-19-oic acid, 17-hydroxy-ent-
[17-hydroxy-ent-isokaur-15(16)-en-19-oic acid]
702 Kaur-15-en-19-oic acid, 17-oxo-ent-
703 Kaur-15-en-17,19-dioic acid, ent-
704 Kaur-9(11),15(16)-dien-19-oic acid, 3a-isovaleryloxy-
[3a-isovaleryloxy-polymnia acid]
705 Kaur-9(11),15(16)-dien-19-oic acid, 3a-isobutyryloxy-ent-
[3a-isobutyryloxy-polymnia acid]
706 Kaur-9(11),15(16)-dien-19-oic acid, 3a-tiglyloxy-ent-
[3a-tiglyloxy-polymnia acid]
707 Kaur-15(16)-en-19-oic acid, 3a-isovaleryloxy-9~-hydroxy-ent-
708 Kaur-15(16)-en-19-oic acid, 3a-isobutyryloxy-9~-hydroxy-ent-
733 Kaurane, 16a,17-epoxy-ent-

709 Kaurane, 3a-angeloyloxy-16a,17-epoxy-ent-
734 Kauran-19-o1, 16a,17-epoxy-ent-
710 Kaurane, 19-ange1oy1oxy-16a,17-epoxy-ent-
711 Kaurane, 3a-angeloy1oxy-19-oxo-16a,17-epoxy-ent-
735 Kauran-19-al, 16a,17-epoxy-ent-
712 Kauran-19-al, 16~,17-epoxy-ent-
713 Kauran-19-oic acid, 16a,17-epoxy-ent-

714 Kauran-19-oic acid, 16~,17-epoxy-ent-
715 Kauran-19-oic acid, 15a-angeloyloxy-16,

17-epoxy-ent- [Perymenium acid]
716 Kauran-19-oic acid, 15a-acetoxy-16,17-epoxy-ent-
717 Kauran-19-oic acid, 15~-angeloyloxy-16,17-epoxy-ent-
718 Kauran-19-oic acid, 15~-tigloyloxy-16,17-epoxy-ent-
719 Kauren-19-oic acid, 12~-hydroxy-16a,17-epoxy-16,

17-dihydro-9(11)-dehydro-ent-
720 Kaurane, 16a-hydroxy-ent- [(-)-kauranol]
1001 Kauran-16~-ol, (-)-
721 Kaurane, 3~-acetoxy-16a-hydroxy-ent-
TABLE 1. (contd.)
Compound:
No. Name
722 Kaurane, 16a-hydroxy-19-acetoxy-ent-
723 Kauran-19-oic acid, 16a-hydroxy-ent-
725 Kaurane, 16a,17-dihydroxy-ent- [17-hydroxy-ent-kauranoll
726 Kaurane, 16a,17,19-trihydroxy-ent-
727 Kaurane, 16a,17-dihydroxy-3-oxo-ent- [Abbeokutonel
851 Kaurane, 16~-hydroxy-ent- [ent-kauran-16~-oll
852 Kaurane, 16~,19-dihydroxy-ent- [ent-kauran-16~,19-dioll
728 Kauran-19-oic acid; 16a,17-dihydroxy-ent-

924 Kauran-19-oic acid, 17-hydroxy-16a-H-ent-
925 Kauran-17,19-dioic acid, 16a-H-ent-
822 Kauran-19-oic acid, 16~,17-dihydroxy-ent-
729 Kauran-17-al, 16~-H-ent-
730 Kauran-17-al, 19-hydroxy-16~-H-ent-
731 Kauran-17-oic acid, 16~-H-ent-
732 Kauran-17-oic acid, 19-hydroxy-16~-H-ent-
736 Kaurane, 16a-acetyl-19-hydroxy-16-desmethyl-ent-

737 Kauran-17,19-dial, 16~-H-ent-
738 Kauran-19-oic acid, 17-hydroxy-16~-H-ent-
739 Kaur-9(11)-en-19-oic acid, 16a,17-dihydroxy-ent-

989 Kauran-19-al-17-oic acid, 16a(-)-
990 Kauran-17,19-dioic acid, 16a(-)-
740 Kauran-17-al, 18-[p-hydroxyhydrocinnamoy1oxy]-ent-
741 Kauran-19-oic acid, 17-isobutyrloyloxy-16~-H-ent-
742 Kauran-19-oic acid, 17-[n-dodecanoyloxy]-16~-H-ent-
743 Kauran-19-oic acid, 17-[n-tetradodecanoyloxyJ-16~-H-ent-
744 Kauran-19-oic acid, 17-[n-hexadecanoyloxy]-16~-H-ent-
745 Kauran-19-oic acid, 17-[n-octadecanoyloxy]-16~-H-ent-
746 Kauran-19-oic acid, 15a,16a-epoxy-17-hydroxy-ent-

747 Kauran-19-oic acid, 11~-hydroxy-15-oxo-16a-H-ent-
TABLE 1. (contd.)
Compound:
No. Name
748 [= 815 = 747]
942 Kaurena1, 9,11-dehydro-ent-
943 Kaur-16-en-19-oic acid, 9(11)-dehydro-15a-cinnamoy1oxy-ent-
850 Kaur-16-en-19-oic acid thujano1 ester, ent-
1255 Kauran-19-a1, 16a-hydroxy-
1256 Rui10pezia acid [16a-Hydroxy-kaur-9(11)-en-19-oic acid]
59. ent-Kaurane, 17-Nor-

749 Kauran-19-oic acid, 17-nor-16-oxo-ent-

752 Kaur-16-ene, 18-nor-ent-
753 Kaur-16-ene, 4~-hydroxy-18-nor-ent- [4-epi-rui1opezio1]
754 Athrixianone, 4-hydroxymethy1-
755 Athrixianone, 4-formy1-
756 Athrixianone, 4-carbomethoxy-
757 Athrixianone, 16,17-dihydro-16,17-epoxy-
758 Atractyligenin
813 Kaurene, 4~,19-epoxy-18-nor-ent-

750 Kaur-16-ene, 19-nor-ent-
751 Kaur-16-ene, 4a-hydroxy-19-nor-ent- [Ruilopezio1]
62. ent-Kaurane, 9,10-Seco-

759 Termina10ic acid
866 Wederegio1ide, 15a-hydroxy-
867 Wederegiolide, 15~-hydroxy-
868 Wederegiolide, 15~-acetoxy-
760 Wedelia-seco-kaurenolide, 9-oxo-

[wede1ia-seco-kaureno1ide]
TABLE 1. (contd.)
Compound:
No. Name
761 Wedelia-seco-kaurenolide, 9a-hydroxy-9-desoxo-
762 Wedelia-seco-kaurenolide, 9~-hydroxy-9desoxo-
763 Wedelia-seco-kaurenolide, lS~-hydroxy-
64. ent-Stachane (ent-Beyerane)

764 Beyer-1S-en-3a-01, ent-
76S Beyer-IS-en-19-o1, ent- [Erythroxylol-A)
766 Beyer-IS-en-18-o1, ent-
767 Beyer-1S-en-3a,19-dio1, ent-
768 Beyer-1S-en-3a,12~-diol, ent-
769 Erythroxylol A-malonate
770 Beyer-1S-en-3a,17-dio1, ent-
817 Beyer-1S-en-12~,19-diol, ent-
771 Beyer-1S-en-17,19-diol, ent- [17-hydroxymonogyno1)
772 Beyer-1S-en-18,19-diol, ent-
774 Beyer-1S-en-19-oic acid, ent- [stach-1S-en-19-oic acid;
beyerenic acid)
773 Beyer-1S-ene, 19-oxo-ent- [20-oxostachene)
77S Beyer-15-en-19-oic acid; 3a-hydroxy-ent-
776 Beyer-15-en-19-oic acid, 3a-tigloyloxy-ent-
777 Beyer-9(11),15-dien-19-oic acid, ent-
778 Beyer-9(11),lS-dien-19-oic acid, 3a-tigloyloxy-ent-
779 Beyeran-18-o1, lS~,16~-epoxy-ent-
780 Beyeran-19-o1, lS~,16~-epoxy-ent [erythroxylo1 A-14,

IS-oxide)
781 Nidoanoma1in
93. ent-Stachane, 19-Nor-

782 Beyer-1S-ene, 4a-hydroxy-19-nor-ent-
6S. Atisirane (Atisane)

TABLE 1. (contd.)
Compound:
No. Name
783 Atis-16-en-19-oic acid
853 Atisan-16a-ol, ent-
854 Atisan-16~-ol, ent-
814 Atis-16-en-19-oic acid, 13-hydroxy-
816 Atis-13-en-3a,16~-diol, ent-
784 Atis-16-en-19-oic acid, 7a-hydroxy-ent- [occidentalic acid)
785 Atisirene acid, 11a-acetoxy-
[11a-acetoxy-atisirene-20-acid)
786 Atisirene acid, 13a-angeloyloxy-
787 Atisirene acid, 13a-isovaleryloxy-
788 Atisirene acid, 13a-isobutyryloxy-
789 Atisirene acid, 7a-acetoxy-9,11-didehydro- [7a-acetoxy-9,
11-didehydroatisirene-20-acid)
790 Atisirene acid, 14~-acetoxy-9,l1-didehydro- [14~-acetoxy-9,
11-didehydro-atisirene-20-acid)
66. Trachylobane
855 Trachyloban-19-al, ent-
791 Trachyloban-19-oic acid
825 Trachyloban-19-oic acid, 15a-acetoxy-
826 Trachyloban-19-oic acid, 15a-angeloyloxy-
827 Trachyloban-19-oic acid; 15a·isovaleryloxy-
893 Trachyloban-19-oic acid, 15a-isobutyryloxy-
792 Trachyloban-19-oic acid, 7a-hydroxy- [Ciliaric acid)
793 Trachyloban-19-oic acid, 11-oxo-
794 Trachy1obanoic acid, 9,11-dehydro-
795 Trachyloban-19-oic acid,
11a-[16'a-hydroxy-ent-kaur-11'-en-19'-oyloxy)-
856 Trachyloban-19-oic acid thujanol ester, ent-
1204 Tachyloban-19-oic acid methyl ester
1259 Trachy1oban-19-oic acid, 7~-hydroxy-
67. Helifulvane
796 Helifulvan-19-o1
TABLE 1. (contd.)
Compound:
No. Name
797 Helifulvan-19-oic acid
798 Helifulvan-19-oic acid, lla-hydroxy-
799 Helifulvan-19-oic acid, lla-acetoxy-
68. Tetrachyrane
800 Tetrachyrin [Zoapatlin]
847 Zoapatlin, 15-oxo-
805 Eupatalbin
806 Eupatoralbin
78. Villanovane
875 Villanovane, 13a,17-dihydroxy-19-isovaleryloxy-
876 Villanovane, 17-acetoxy-13a-hydroxy-19-isovaleryloxy-
877 Villanovane, 13a,17-dihydroxy-19-(3-methylvaleryloxy)-
878 Villanovane, 17-acetoxy-13a-hydroxy-19-(3-methylvaleryloxy)-
879 villanovane, 17-acetoxy-13a-hydroxy-3a-isovaleryloxy-
880 Villanovane, 17-acetoxy-13a-hydroxy-3a-(3-methylvaleryloxy)-
894 Villanovane, 3a,15a-dihydroxy-
69. Lycoctonine
801 Lycaconitine, methyl-
802 Lycoctonine [royline; roylene]
803 Lycoctonine, anthranoyl-
VIII. Undetermined Stereochemistry

79. Inulaefane
804 Inulaefol
84. Hebeclinane (9,lO-Seco-Labdane)

940 Jhanic acid
999 Hebeclinolide
TABLE 2. The Substitutional Patterns of the Diterpenes Reported from the Compositae
(Asteraceae) .
Compound:
No. Substituents
1. Gerany1nero1
17 18
19 20
1 l(OH)
2 1 ( OH) ; 18 ( OH )
3 1 ( OH) ; 20 ( OH )
4 1(OH);17(OH);20(OH)
5 1(=0)
6 18(=0,OH);1(OH);16(OH)
7 13(=0);1(OH);19(OH)
8 16(=0);1(OH);19(OH);20(OH)
15 1(OH);12(OH);20(OH);19(OAc)
984 1(OH);20(OH);19(OAc)
948 1(OH);8(OH);12(OH);19(OH)
957 1(OH);16(OH);18(OH);19(OH)
978 12(=0);1(OH);19(OH)
1002 19 ( =0, OH) ; l( OH )
1003 19(=0,OH);1(OAc)
1109 1(OH);17(OH);18(OH)
1110 1(OH);17(OH);18(OH);20(OH)
1111 1(=0);12(=0)
1112 1(OH);16(OH);20(OH);18(OAc);19(OAc)
1113 1(OH);16(OH);18(OAc);19(OAc);20(OAc)
1114 1(OH);16(OH);20(OH);18(OAc)
Table 2. Substitutional Patterns 61
TABLE 2. (contd.)
Compound:
No. Substituents
1115 1(OH)i16(OH)i20(OH)i19(OAc)
1116 1(OH)i9(OH);17(OH)
1117 1(OH);9(OH);17(OH);19(OH)
18 19 20
14 2(3)Z;6(7)Z;10(11)E;14(15);19(=O,OH);18(=O);1(OH)
949 2(3)Z;10(11)E;14(15);6(-O-)7;1(OH);8(OH);
12 ( OH) ; 19 ( OH )
979 2(3)Z;10(11)E;14(15);12(=O);1(OH);19(OH);6(-O-)7
1004 2(3)Z;6(7)Z;10(11)E;14(=O);1(OH);15(OH);19(OH)
1005 2(3)Z;6(7)Z;10(11)E;14(=O);15(OH);1(OAc);19(OAC)
1095 2(3)E;14(15);12(=O);1(OH);20(OH);6(-O-)7
1096 2(3)E;13(14)E;12(=O);1(OH);15(OH);20(OH);6(-O-)7
1020 2(3)E;6(7)E;14(15);1(OH);9(OH);20(OAc)
2. Geranylgeraniol
14 12 10 B 8 2
18 4
17 18 19 20
TABLE 2. (contd.)
Compound:
No. Substituents
11 1(OH);12(OH);19(OH)
12 12(OH);19(OH);1(OAe)
13 l(OH) ;16(OH)
17 1(=0)
18 1(=0) ;4u(OH)
19 17 ( =0, OH) ; 1 (OAe )
954 18(=0,OH);1(OH)
1118 1(OH);17(OH);18(OAe)
1119 1(=0) ;12(=0)
14 12 10 8 8
16 2(3)E;6(7)E;10(11)E;1(OH);4(OH);14(OH);15(OH)
20 6(7)E;10(11)E;13(=O);1(OH)
21 2(3)E;6(7)Z;14(15);12(=O);1(OH);19(OH)
22 2(3)E;6(7)Z;10(11)E;14(15);1(OH);12(OH);18(OH)
1120 2(3)E;6(7)E;10(11)E;14(15);18(=0);19(=0);1(OH)
3. Geranyllinalool
8 6 4 OH 2
17 It 20
18
23
24 13(OH)
25 13(OAe)
TABLE 2. (contd.)
Compound:
No. Substituents
26 9(OH)
27 9(OAe)
28 5(OH)
29 5 ( OH) ; 9 ( OAe )
30 5 (OAe) ; 9 (OAe)
31 5 ( OH) ; 13 ( OAe )
32 12(=0)
33 13(=0)
1121 13(OAe)
14 12 10 8 8 4 OH 2
18
~
17 18
It 20
34 13(=0);14(-0-)15
35 13 ( 14 ) E ; 15 ( OH )
36 13(14)E;15(17)
37 14 ( OH) ; 15 ( OH )
38 5(OH);14(OH);15(OH)
39 14(OH);15(OH);9(OAe)
18
14 12 10 II 8 OH 2
4
~'
17 111 20
"
1122 6(7)Z;10(11)Z;14(15);12(=O)
1123 6(7)Z;13(14)E;12(=O);15(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
4. Phytol-Derived
14 12 10 8 6 2
18 19 20
59 1(2)i3(20)
21
17 18
19 20
9 6(7)Zi10(11)Ei14(21)i1(OH)i12(OH)i19(OH)i
20(OH)
10 6(7)Zi10(11)Ei14(21)i1(OH)i12(OH)i20(OH)i
19(OAc)
980 6(7)Zi10(11)Ei13(14)Ei12(=O)i1(OH)i19(OH)
981 10(11)Ei13(14)Ei12(=O)i6(-O-)7il(OH)i
19(OH)
982 6(7)Zi10(11)Ei14(21)i12(=O);1(OH)i19(OH)
983 10(11)Ei14(21)i12(=O)i1(OH)i19(OH)i6(-O-)7
1094 14(21)i12(=O)il(OH)i20(OH)i6(-O-)7
10 9
40 1(OH)i 6 (OH)
TABLE 2. (contd.)
Compound:
No. Substituents
41 6(OH);1(OAc)
42 1(OH);6(OH)j17(OH)
43 1(OH)j6(OH)j17(OAc)
1124 1(OAc)j6(OAc)
6. Acanthoaustralane-6,11-Epoxide
9 a
17
4
~ 16
13 11
5
2
20
44 1(OH)jl0(OH)j17(OAc)
45 1(OH);10(OH)j17(OH)
8 19
9
10 4
17~
~ r0 13
12
11
18
16 20
0
46 1(OH)j7(OH)j17(OH)
47 1(OH)j7(OH)j17(OAc)
48 7 ( OH) ; 1 ( OAe )
TABLE 2. (contd.)
Compound:
No. Substituents
14 12
18
19 20
49 14(15) ;l(OH)
50 14(15);1(OH);19(OAc)
51 13(14)E;1(OH);15(OOH)
52 13 ( 14 ) E ; 1 ( OH) ; 15 ( OH )
53 15(17);1(OH);14(OOH)
54 15(17);1(OH);14(OH)
9. OXepane
5 4
18
18 19
17
55 14(15);1(OH);6u(OH)
56 13(14)E;6(OH);15(OH);1(OAc)
57 13(14)E;1(OH);6u(OH);14(Me)
1097 1(OH);6u(OH);14(CH2)
1098 13(14)E;1(OH);6u(OH);15(OH)
1099 15(16);1(OH);6u(OH);14(CH3)
TABLE 2. (contd.)
Compound:
No. Substituents
86. Melcanthane
18 14 12
~~1
I 18
19
17
1006 2(3)Z;10(11)Z;14(15);1(OH);6(OH);7(OH);17(OAc)
10. Mikanofurane
18
17 18 19
58
11. Centipedane
8 8 4 2
~1
20
o
17 19
60 18(=0,OH)
61 18(OH);19(OH)
1125 12(=0)
1126 12 (OH)
1127 12(=0);13(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
10 8 8 4 2
~,
20
o
17 Ii
1128 6(7)E;10(11)E;13(14)E;12(=O);1S(OOH)
12. Geranylgeraniol-l,20-Lactone
.~
14 12 10 8 8 4 2
I. 20
17 18
62 14(1S)i 17 (=O,OH)
63 14(15);17(=O,OMe)
64 14(OH);15(OH)
1129 14(15);12(=0)
1130 14(15);18(=0,OH);17(OH)
1132 14(15);18(=0,OH);17(OAc)
to 8 e 4 2
17 11 I.
1131 2(3);6(7)Ei10(11)Ei14(1S)i18(=O,OH)i 1 (=O)i17(OH)
1133 2(3)i14(lS)i20(=O)i17(OH)i19(OH)i18(OAC)
1134 2(3)i14(15);20(=O)i17(OH)i18(OAc);19(OAc)
1135 2(3)i6(7)Ei10(11)Zi14(15);18(=O,OH)i20(=O);17(OH)
1136 2(3);6(7)E;10(11)Z;14(15);18(=O,OH);20(=O);17(OAc)
TABLE 2. (contd.)
Compound:
No. Substituents
1137 6(7)E;10(11)E;14(15);12(=O);1~(-O-)2~;20(=O)
4 20
14 12 10 8
'~'
17 18 19
65 2(3);7(8)E;10(11)E;14(15)E;16(OH)
66 2(3);7(8)E;10(11)E;14(15)E;16(=O)
67 2(3);7(8)E;10(11)E;16(=O,OH)
68 1(6);2(3);10(11)E;14(15)
69 1(6);2(3);14(15);10a(OH);11(OH)
71 1 ( 6 ) ; 2 ( 3 ) ; 4 ( 5 ) ; 14 ( 15 ) ; lOa ( OH) ; 11 ( OH )
70 1(6);2(3);4(5);10(11)E;14(15)
72 14(15);3~(-O-O-)6~;10a(OH);11(OH)
1101 14(15);3a(-O-O-)6a;10a(OH);11(OH)
1138 2(3)j10(11)Ej14(15)j7(OH)
14. Isocembrene
18
11 10
16
19
17
20
73 15(OH)
TABLE2. (contd.)
Compound:
No. Substituents
18
17
74 1(OH);10a(OH);15(OH);19(OH)
75 1(OH);10a(OH);15(OH);19(OAc)
II. Normal-Bicarbocyclics and Derivatives

16. Normal-Labdane
12 14
18 18
79 8a ( OH) ; 15 ( OH )
80 7~(OH);8a(OH);15(OH)
958 15 ( =0 , OH) ; 8a ( OH )
1139 8a(OH);15(OH)
12 14
18 18
81 8a(OH);15(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
86 7(8);13~(OH);14~(OH);15(OH);14a(H)
87 8(9) ;13~(OH) ;14~(OH) ;15(OH) ;14a(H)
124 7(8);15(=O,OH);2a(OH);3a(OH)
125 7(8);15(=O,OH);2a(OH);3a(OMebut-2-0H)
129 7(8);15(=O,OH);3(=O)
1140 8(17);15(=O,OH);7a(OH);19(OH)
1141 8(17);15(=O,OH);7a(OH);19(OAc)
1142 8(17);15(=O,OH);7~(OH);19(OH)
12 14
18 18
76 8(17);13(14)E;15(OH)
77 8(17);13(14)E;3a(OH);15(OH);7a(O~-Ga1)
78 8(17);13(14)Z;2a(OH);15(OH)
1103 13(14)E;8a(OH);15(OH)
82 12(13)E;9a(OH);14a(OH);15(OH);8a(H)
83 12(13)E;9a(OH);14a(OH);15(OAc);8a(H)
84 12(13)E;9a(OH);14a(OAc);15(OAc);8a(H)
85 8(17);13(-O-)14;15(OH)
88 8(17);14(OH);15(OH)
89 8 ( 17 ) ; 13 ( OH) ; 14 ( OH) ; 15 ( OH )
90 8(17);14(OH);15(OAc)
993 7(8);3a(OH);15(OH);13~(H)
994 7(8);15(02-Mebut);3a(OH);13~(H)
995 8(17);3a(OH);7a(OH);15(OH);13~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
91 8(17)i13(OH)i14(OH)i15(OAc)
92 8(17)i15(OH)i14(OAc)
93 8(17)i 13 (OH)i14(OPro)i15(OAc)
94 12(13)Ei9a(OH)i14~(OH)i15(OH)i8a(H)
97 7(8)i13(14)Zi15(=O,OH)i12(=O)i17(=O)i2a(OAng)i3a(OAng)
98 13(14)Zi 15 (=OiOH) i8a(OH) i7a(O-trans-Cinn) i2(OAng or
OMebut-2-0H)i3(OAng or OMebut-2-0H)
99 13(14)Zi15(=O,OH)i8a(OH)i7a(O-cis-Cinn)i2(OAng or
OMebut-2-0H)i 3(OAng or OMebut-2-0H)
100 7(8)i13(14)Zi 15 (=O,OH)i2(OAng)
116 7(8)i13(14)Zi15(=O,OH)i3a(OH)
101 7(8)i13(14)Z;15(=O,OH);18(OAng)
102 7(8)i13(14)Zi15(=O,OH)i18(OTig)
103 7(8)i13(14)Z;15(=O,OH);2a(OH);3a(OAng)
104 7(8);13(14)Zi15(=O,OH)i2a(OH)i3a(O-trans-Cinn)
105 7(8);13(14)Zi 15(=O,OH);2a(OH);3a(O-cis-Cinn)

106 7(8);13(14)Z;15(=O,OH)i 2a (OH)i 3a(OAng)
107 7(8)i13(14)Zi15(=O,OH);3a(OH)i2a(OAng)
108 8(17)i13(14)Z;15(=O,OH)i2a(OH);3a(OAng)
109 8(17)i13(14)Zi15(=O,OH);3a(OH)i2a(OAng)
110 7(8);13(14)Z;15(=O,OH);19(=O,OH)
III 8(17);13(14)E;15(=O,OH)
112 7(8);13(14)E;15(=O,OH);2a(OTig)
113 7(8)i13(14)E;15(=O,OH);3~(OAC)
114 7(8);13(14)E;15(=O,OH);3a(OH)
115 7(8)i13(14)E;15(=O,OH);3~(OH)
117 7(8)i13(14)E;15(=O,OH);3(=O)
118 7(8);15(=O,OH)
991 7(8)i15(=O,OH)i3a(OH);13~(H)
992 7(8);15(=o,OMe);3a(OH);13~(H)
119 7(8);15(=O,OH)i3a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
120 7(8);15(=0,OH);3~(OH)
121 15(=0,OH);8u(OH)
871 7(8);2u(OH);15(OH)
872 7(8);2u(OH);15(OCoum)
873 7(8);2u(OH);15(03-Me-Coum)
874 7(8);2u(OH);15(p-OH-Cinn)
122 7(8);15(=0,OH);18(OAng)
123 7(8);15(=0,OH);18(OTig)
126 7(8);15(=0,OH);2u(OH);3u(OAng)
127 7(8);15(=0,OH);2u(OH);3u(0-trans-Cinn)
128 7(8);15(=0,OH);2u(OH);3u(O-cis-Cinn)
870 7(8);15(=0,OMe);3~(OAc);2u(OSen)
130 7(8);13(14)E;15(=0,OH);18(=0,OH)
977 8(17);19(=0,OH);15(=0);13u(H)
131 7(8);15(=0,OH);18(=0,OH)
132 8(17);12(13)E;14(15)
133 8(17);12(13)E;14(15);3u(OH)
134 8(17);12(13)E;14(15);3~(OH)
135 8(17);12(13)E;14(15);3~(OAc)
136 8(17);12(13)E;14(15);3(=0)
959 8(17);15(=0,OH);2~(OAc)
137 8(17);12(13)E;14(15);18(=0,OH)
1104 8(17);12(13)E;14(lS);19(=0,OH)
138 8(17);12(13)E;14(15);18(=0,OH);7u(OAc)
139 12(13)Z;14(15);8u(OH)
140 12(13)Z;14(15);7~(OH);8u(OH)
141 12(13)E;14(15);7~(OH);8u(OH)
142 12(13)E;14(15);6u(OH);7~(OH);8u(OH)
143 12(13)E;14(15);7~(OH);8u(OH);6u(OAng)
TABLE 2. (contd.)
Compound:
No. Substituents
144 12(13)E;14(15);6~(OH);8a(OH)
145 12(13)E;14(15);8a(OH);7~(OAC)
146 12(13)E;14(15);6~(OH);7~(OH);8a(OH)
147 12(13)E;14(15);6~(OH);8a(OH);19(OH)
148 12(13)E;14(15);6~(OH);8a(OH);7~(OAc)
149 12(13)E;14(15);8a(OH);1~(OAc);19(OArac)
150 12(13)E;14(15);8a(OH);1~(OAc);19(OCoum)
151 12(13)E;14(15);8a(OH);1~(OAc);19(O-cis-Coum)
152 12(13)E;14(15);9a(OH);19(OH);8a(H)
153 14(15);8a(OH);13~(OH);6a(OAng)
1102 14(15);8a(OH);13~(OH)
996 8(17);14(15);13~(OH)
154 7(8);14(15);2(OH);13(OH)
1105 7(8);14(15);13~(OH)
1106 7(8);14(15);3~(OH);13~(OH)
1107 7(8);14(15);3(=O);13~(OH)
155 13(16);14(15);8a(OH)
156 13(16);14(15);6~(OH);8a(OH);7~(OAc);12~(O-OH)
157 13(16);14(15);6~(OH);8a(OH);7~(OAc);12a(O-OH)
158 7(8);13(16);14(15);6(=O);9a(OH);15(-O-)16
159 7(8);13(16);14(15);18(=O,OH);17(OH);15(-O-)16
160 7(8);13(16);14(15);17(=O,OH);6a(02-Mebut);15(-O-)16
161 7(8);13(16);14(15);17(=O,OH);6a(Oi-But);15(-O-)16
162 7(8);13(16);14(15);17(=O,OH);6a(Oi-Val);15(-O-)16
163 8(17);13(16);14(15);19(=O,OH);7a(OH);15(-O-)16
1021 12(13)Z;14(15);8a(OH);7~(OAC)
1022 12(13)E;14(15);6a(OH);8a(OH);7~(OAC)
1023 12(13)Z;14(15);6a(OH);8a(OH);7~(OAc)
1024 13(14)Z;15(=O,OH);8a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
1143 8(17);15(=O,OH);7a(OH)
1144 8(17);15(=O,OH);7a(OAc)
1145 7(8);15(=O,OH);19(OH)
1146 7(8);15(=O,OH);3~(OH)
1147 8(17);12(13)E;14(15);19(=O,OH)
1151 13(16);14(15);8a(OH);3~(OAc)
12 14
20
15
o
18 ~,J
4'~
J' 2'
95 7(8);14(15);19(=O);13~(OH);2'a(OH);41~(OH);3'~(OTig)
96 7(8);14(15);19(=O);13~(OH);2Ia(OH);31~(OH);4'~(OH)
1148 7(8);14(15);19(=O);13~(OH);31~(OH);4Ia(OH);2'a(OAc)
1149 7(8);14(15);19(=O,OMe);13~(OH);3'~(OH);4Ia(OH);2'a(OAc)
1150 7(8);14(15);19(=o,OMe);13~(OH);2Ia(OH);31~(OH);4'a(OH)
12 14
1152 13(16);14(15);8a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
17. Grindelane
14
o
1a 18
165 8(17);7a(OH)
166 6(7);8(17)
167 7(8) ;13(5)
955 7(8);13(R)
168 7(8);la(OH)
169 7(8);3(3(OH)
170 7(8);6a(OH)
172 7(8);6(3(OH)
173 7(8);17(OH)
171 7(8);6a(OCHO)
174 7(8);17(OAc)
175 7(8);17(OPro)
176 7(8);17(Oi-But)
177 7(8);17(Oi-Val)
178 7(8);17(02-Mebut)
179 7(8);17(OMe)
180 7(8);19(OH)
181 7(8);19(OAc)
182 7(8);19(Oi-Val)
183 7(8);19(Oi-But)
TABLE 2. (contd.)
Compound:
No. Substituents
184 7(8);19(02-Mebut)
185 7(8);19(OSucc)
186 7(8) ;19(=0)
187 7(8);19(=0,OH)
188 7(8);18(OH)
189 7 (8) ; 6 (=0)
190 7(8);6(=0);19(OAc)
191 713(-0-)813
192 7a( -0- )8a
1035 7(8);3a(OH)
1036 8(17);713(OH)
1153 7(8);19(=0,OH);15(=0,OMe)
12 14
20 ~15
0
2
III II
0
193
12 18
18 Ie o
194
TABLE 2. (contd.)
Compound:
No. Substituents
14
12
15 0
18 18
1060
14
12
o
2
14 12'
18 la
3
956
11 ,.
1187 7(8);2'a(OH);3'~(OH);4'~(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
18. Hormal-Labdane-8,13-Epoxide
18 18
272 14(15)
195 14(15);19(OH)
196 14(15);19(OAc)
197 14(15);1~(OH);19(OH)
198 14(15);1~(OH);19(OAc)
199 14(15);1~(OAc);19(OAc)
200 14(15);3~(OAc)
201 14(15);3~(OH);18(OBenz)
964 15(=0)
3 17
18 111
273
202 19(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
19. Normal-Labdane-8,12-Epoxide 11
2 Iii
17
.3
18 111
203 15 ( OH) ; 16 ( OH )
204 15 ( OH) ; 16 ( OAc )
205 15 ( OAc ) ; 16 ( OAc )
206 16 ( =0) ; 15 ( OH)
207 1 5 ( =0) ; 1 6 ( =0 )
210 15(OH)
1!5
211 15(=0,OH)
111
18 111
212 15 ( =0) ; 16 ( =0 ) 111
213 14(=0) ;15(=0);16(OAc)
20
2
17
.3
111 I.
TABLE 2. (contd.)
Compound:
No. Substituents
208 15(OH);16(OH);13a(-0-)14a;14~(H)
209 15(OH);16(OH);13~(-0-)14~;14a(H)
20. Hormal-Labdane-15,16-Lactone
12 14
o
2
II ..
164 7(8);18(=0,OH)
965 7(8);17(OH)
15
966 7(8);17(=0)
21. Hormal-Labdane-20,12-Lactone
•
II 18
214 1(=0);5a(OH);9a(OH);8~(H)
o
22. Hormal-Labdane Spiroketal
2 17
8
18 111
215 7(8);13(14);2a(OAng);3a(OAng)
TABLE 2. (contd.)
Compound:
No. Substituents
216 7(8);13(14);17a(OH);2a(OAng);3a(OAng)
217 7(8);13(14);17~(OH);2a(OAng);3a(OAng)
218 7(8);13(14);2a(OH);3a(OAng)
1. 14
111 11
938 3a(OH);7a(OAc);8~(H)

12 14
15
2
I. 18
219 6(7);14(15);12(13)E;19(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
24. Hormal-Labdane, 3,4-Seco-
II I.
IS
o
II
220 7(8);15(=O,OH)

t2 t4
o
te ti
V;y
• -:.
-:. t7
223 o
89. Grindelane, 19-Nor-
t2 14
18
221 7(8);15(=O,OH);4a(OH)
222 7(8);15(=O,OH);4a(OCHO)
1154 7(8);15(=O,OMe);6(=O);4a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
26. Grindelane, 8,17-Bis-Nor-8,9-Seco-
18 11
224
27. Normal -Labdane-20,l2-Lactone, 5,10-Seco-
18 11
225 5(=O);6a(OH);1(-O-)10
226 5(=O);6a(OAng);1(-O-)10
227 5(=O);6a(Oi-But);1(-O-)10
228 5(=O);6a(02-Mebut);1(-O-)10
229 5(=O);6(Oi-Val);1(-O-)10
230 5(OH);6a(OAng);1(-O-)10
TABLE 2. (contd.)
Compound:
No. Substituents
100. Normal-Labdane, 14,15-Bis-Nor-
12 11
1155 11(12)E;13(=O);8a(OH)
1157 11(12)E;13(=O);6a(OH);7~(OH);8a(OH)
1158 11(12)E;13(=O);7~(OH);8a(OH);6a(OAc)
1159 11(12)E;13(=O);6a(OH);8a(OH);7~(OAc)
1160 11(12)E;13(=O);7~(OH);8a(OH)
101. Normal-Labdane, 13,14,15,16-Tetranor-
HI 19
1156
87. Hexanorlabdane
2
OH
J
111
TABLE 2. (contd.)
Compound:
No. Substituents
28. Relhaniane
12 14
18 III
231 1(10);13(14)E;15(=O,OH);2(=O);8~(H)
232 5(6);19(=O,OH);15(OH);10u(H);8u(H)
12 14
18 111
233 5(6);13(16);14(15);19(=O,OH);8u(H)
234 5(6);13(14);19(=O,OH);16(=O);8u(H)
235 5(6);13(14);19(=O,OH);15(=O);8u(H)
29. ~-Normal-Clerodane
(No proven structures of this type)

12 14
111
18
TABLE 2. (contd.)
Compound:
No. Substituents
HI
255 1(2);3(4);18(=O,OH);8~(H) [Revised to 9a-Mej

256 1(2);3(4);18(=o,OMe);8~(H) [Revised to 9a-Mej
12 14
11.1
238 3(4);13(16);14(15);19(OH);15(-O-)16;8~(H)
253 3(4);13(14);15(=O);19(OH);8~(H)
254 3(4) ;13(14) ;16(=0) ;19(OH) ;8~(H)
257 3(4);15(=0,OH);8a(H)
258 3(4);13(14);15(=0);6~(OAng);15(-0-)16;8~(H)
259 3(4);13(14);15(=O);6~(OTig);15(-0-)16;8~(H)
260 13(14);15(=0);3~(-0-)4~;6~(OAng);15(-O-)16;8~(H)
261 13(14);15(=0);3a(-0-)4a;6~(OTig);15(-0-)16;8~(H)
262 3(4);13(14);6(=0);15(=0);15(-O-)16;8~(H)
263 3(4);13(14);15(=O);2a(OH);6~(OAng);15(-O-)16;8~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
264 3(4)i13(14)i15(=0)i2a(OH)i6~(OTig)i15(-0-)16i8~(H)
265 3(4)i13(14)i6(=0)i15(=0)i2~(OH)i15(-0-)16i8~(H)
266 13(14)i15(=0)i3~(OH)i4a(OH)i6~(OAng)i15(-0-)16i8~(H)
267 13(14)i15(=0)i3~(OH)i4a(OH)i6~(OTig)i15(-0-)16i8~(H)
268 13(14)i3(=0)i15(=0)i6~(OAng)i15(-0-)16i8~(H)
269 13(14)i3(=0)i15(=0)i6~(OTig)i15(-0-)16i8~(H)
545 3(4)i13(14)i15(=0)i6~(OH)i15(-0-)16i8~(H)
546 3(4)i13(14);15(=0)i6~(OAC)i15(-0-)16i8~(H)
551 13(14)i15(=0)i2a(OH)i3a(-0-)4ai15(-0-)16i8~(H)
552 13(14)i15(=0)i6~(OAng)i3a(-0-)4ai15(-0-)16i8~(H)
553 13(14)i15(=0)i3~(-0-)4~i6~(OAC)i15(-0-)16i8~(H)
988 13(14)i15(=0)i3~(-0-)4~i6~(OTig)i15(-0-)16i8~(H)
239 3(4)i13(16)i14(15)i19(=0,OH)i15(-0-)16i8~(H)
240 3(4)i13(16)i14(15)i19(=0)i15(-0-)16i8~(H)
241 3(4)i13(16)i14(15)i19(OH)i15(-0-)16i8~(H)
242 3(4)i13(16)i14(15)i18(OH)i19(OH)i15(-0-)16i8~(H)
243 3(4)i13(16)i14(15)i18(=0)i19(=0)i15(-0-)16i8~(H)
244 3(4)i13(16)i14(15)i19(=0,OH)i18(OAng)i15(-0-)16i8~(H)
246 3(4)i13(16)i14(15)i18(-0-)19i19(OH)i15(-0-)16i8~(H)
247 18(-0-)19i3(-0-)4i19(OH)i15(-0-)16i8~(H)
270 13(14)i15(=0)i3a(Cl)i4~(OH)i19(OMe)i15(-0-)16i
18(-0-)19
556 13(14)i15(=0)i3~(-0-)4~i15(-0-)16
557 13(14)i15(=0)i3(-0-)4i7~(OAng)i15(-0-)16
1025 3(4)i14(15)i2(=0)i13~(OH)i6~(OAc)i8~(H)
1062 3(4) i13(16) i14(15) i19(=0) i15(-0-)l6i8~(H) i

1063 3(4)i13(16)i14(15)i18(=0)i19(=0)i15(-0-)16i8~(H)
1064 3(4)i13(16)i14(15)i19(OH)i15(-0-)16i8~(H)
1065 3(4) i13(16) ;14(15) i18(OH) i15(-0-)16i8~(H)
1066 3(4)i13(16)i14(15)i18(=0)i15(-0-)16i18(-0-)19i8~(H)
1067 3(4)i13(16)i14(15)i19(OH);15(-0-)16i18(-0-)19i8~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
1068 13(16);14(15);19(OH);3a(-O-)4a;15(-O-)16;
18(-O-)l9;8[3(H)
1083 3(4);13(14);15(=O);6a(OH);18(OH);15(-O-)16;8a(H)
1084 3(4);13(14);15(=O);18(OH);19(OH);15(-O-)16;8a(H)
1085 3(4);13(14);15(=O);18(=O);15(-O-)16;18(-O-)19;8a(H)
1086 3(4);13(14);15(=O);19a(OH);15(-O-)16;
18(-O-)19;8a(H);19[3(H);
1087 13(14);15(=O);18[3(OH);19a(OH);3a(-O-)4a;15(-O-)16;
18(-O-)19;8a(H);18a(H);19[3(H)
1088 13(14);15(=O);18(=O);19a(OH);3a(-O-)4a;
15(-O-)16;18(-O-)19;8a(H);19[3(H)
1089 13(14);15(=O);19a(OH);3a(-O-)4a;15(-O-)16;
18(-O-)19;8a(H);19[3(H)
1090 13(14);15(=O);3a(OH);4[3(OH);19a(OH);15(-O-)16;
18(-O-)19;8a(H);19[3(H)
1091 3(4);13(14);15(=O);19(=O,O-Arab);15(-O-)16;8a(H)
1092 3(4);13(14);15(=O);18(=O);2[3(OH);15(-O-)16;
18(-O-)6a;8a(H)
2
o
J
11
947
72. Chrysolane
20
2
0
l
I. I'
271
TABLE 2. (contd.)
Compound:
No. Substituents
III. Hormal-Tricarbocyclics and Derivatives

32. Sandaracopimarane (Hormal-Pimarane)
115 111
274 8(14);15(16)
927 8(14);15(16);7a(OH)
928 8(14);15(16);1~(OH);7a(OH)
929 8(14);15(16);7a(OH);1~(OAc)
930 8(14);15(16);1~(OH);7a(OAc)
931 8(14);15(16);1~(OH);11a(OH)
932 8(14);15(16);1~(OAc);11a(OAc)
933 8(14);15(16);1~(OH);11a(OH);7a(OAc)
934 8(14);15(16);7a(OH);1~(OAc);11a(OAc)
935 8(14);15(16);1~(OAc);7a(OAc);11a(OAc)
936 8(14);15(16);6(-O-)7;1~(OAc);11a(OAc)
937 8(14);15(16);7(=O);1~(OAc);11a(OAc)
275 7(8);15(16)
276 15(16);8~(OH)
277 15(16);6~(OH);8~(OH)
278 15(16);8~(OH);6~(OAc)
279 15(16);8~(OH);11a(OH)
280 15(16);8~(OH);11a(OSen)
TABLE 2. (contd.)
Compound:
No. Substituents
281 15(16);8~(OH);11a(OTig)
282 15(16);8~(OH);11~(OAc)
283 15(16);11(=O);8~(OH)
284 15(16);8~(OH);12~(OAc)
285 15(16);8~(OH);18(OH)
286 15(16);8~(OH);20(OH)
287 15(16);20(OH);8~(-O-)20
288 15(16);8~(OH);11a(OH);12~(OH)
289 15(16);8~(OH);12~(OH);11a(OAc)
290 15(16);8~(OH);12~(OH);11a(OSen)
291 15(16);8~(OH);12~(OH);11a(OTig)
292 15(16);8~(OH);11a(OH);12~(OAc)
293 15(16);8~(OH);11a(OH);12~(OCoum)
294 15(16);8~(OH);11a(OAc);12~(OAc)
295 15(16);8~(OH);12a(OH);11~(OAc)
296 15(16);11(=O);8~(OH);12a(OH)
297 15(16);11(=O);8~(OH);12a(OAc)
298 15(16);6~(OH);8~(OH);11a(OH)
299 15(16);8~(OH);11a(OH);6~(OAC)
300 8(14);15(16);18(=O,OH)
301 7(8);15(16);18(=O,OH)
302 8(14);15(16);18(=O,OH);3~(OAc)
807 8(14);3~(OH);15(OH);16(OH);17(OH)
303 7(8);15(16);18(=O,OH);3~(OAC)
921 8(14);19(=O,OH);6~(OH);15(OH);16(OH)
304 7(8);3a(OH);15(OH);16(OH)
305 7(8);9a(OH);15(OH);16(OH)
922 8(14);15(OH);16(OH);6~(OG1u)
923 8(14);6a(OH);15(OH);16(OH);18(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
10
1. II
891 15(16);8~(OH);5a(H);5a(H)
306 7(8);3a(OH);15(OH);16(OH);19(OH);5a(H) [Revised to

rosane]
307 7(8);3a(OH);9a(OH);15(OH);16(OH);5a(H) [Revised to
rosane]
308 5(6);3(OH);15(OH);16(OH);19(OH)
34. Cassane 12 lS
18
18 18
310 12(13);15(16);11(=O);2a(OH)
311 12(13);15(16);11(=O);1~(OH);2a(OH)
312 12(13);11(=O);1~(OH);2a(OH)
35. Rosane 17
12
1S
2
18
18 18
TABLE 2. (contd.)
Compound:
No. Substituents
306 5(6);3a(OH);15(OH);16(OH);19(OH);10a(H)
307 5(6);3a(OH);15(OH);16(OH);10a(H)
313 5(6);3~(OH);15(OH);16(OH);10a(H)
314 5(6);3~(OH);15(OH);16(OH);18(OH);10a(H)
315 5(6);3(=O);15(OH);16(OH);10a(H)
881 15(16);5~'OH);10a(H)
882 15(16);5~(OH);18(OH);10a(H)
883 15(16);5~(OH);18(OAc);10a(H)
884 15(16);3a(OH);5~(OH);10a(H)
885 15(16);5~(OH);18(OTig);10a(H)
886 15(16);3a(OH);5~(OH);18(OH);10a(H)
887 5(6);15(16);3a(OH);18(OH);1~(H)
888 5(6);15(16);18(OH);3a(OAc);10a(H)
889 5(6);15(16);3a(OH);18(OAc)
890 1(10);15(16);18(=O,OH)
1161 5(6);14(OH);15(OH);3~(OAc);18(OAc)
1162 5(6);14(OH);15(OH);18(OH);3~(OAc)
36. Sandaracopimarane, 19-Nor-13-Epi-
17
12
15
2
18
309 4(5);3(=O);15(OH);16(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
37. Normal-Abietane
17
1.
2
.)
1. 18
316 7(8);13(14);2a(OAc)
317 7(8);13(14);3~(OH)
318 7(8) ;13(14) ;3(=0)

319 8(9);11(12);13(14);12(OH)
320 8(9);11(12);13(14);7(=0);11(OH);14(OH);12(OMe)
321 8(9);12(13);11(=0);14(=0);12(OH)
322 6(7);8(9);12(13);11(=0);14(=0);12(OH)
323 8(9);12(13);11(=0);14(=0);12(OH);7a(OAc)
324 8(9);12(13);7(=0);11(=0);14(=0);12(OH)
1072 8(14);6a(OH);13(OH);7a(OSen)
1073 8(14);7a(OH);13(OH);6a(OSen)
1074 8(14);7a(OH);13(OH)
111
4 = H
•
18
1163 8(9);12(13);11(=0);14(=0);7a(OH);12(OH);20(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
94. Stevisalane
12 14
11~
H
-
-HI 15
2 17
II
= 19
18
1026 14(15);2(=O);6~(OH);13~(OH);4~(H);8~(H)
73. Normal-Stachane 17
2 16
18 19
325 15(16);18(=O,OH)

38. ent-Labdane
12 14
HI
TABLE 2. (contd.)
Compound:
No. Substituents
326 8(17);13(14)E;15(OH)
848 8(17);13(14)E;2u(OH);15(OH)
327 8(17);13(14)E;15(Obern)
849 8(17);13(14)E;2(=0);15(OH)
328 8(17);13(14)E;15(OH);7~(OAc)
844 8(17);13(14)E;15(OH);18(OH);3u(OAng)
329 8(17);13(14)E;18(=0,OH);15(OH)
330 8(17);13(14)E;18(=0,OH);15(OAc)
331 8(17);13(14)E;15(=0);2u(OH)
332 8(17);13(14)Z;15(=0);2u(OH)
333 8(17);13(14)E;2(=0);15(=0)
334 8(17);13(14)Z;2(=0);15(=0)
335 8(17);13(14)E;15(=0,OH)
336 8(17);13(14)Z;15(=0,OH)
337 8(17);13(14)Z;15(=0,OH);3u(OH)
338 8(17);13(14)Z;15(=0,OH);3u(OH);7u(OH)
339 13(14)Z;15(=0,OH);17(=O);3u(OH);8~(H)
340 13(14)Z;15(=0,OH);17(=0);3u(OH);8u(H)
341 13(14)Z;15(=0,OH);3(=0);17(=0);8~(H)
342 13(14)Z;15(=O,OH);3(=0);17(=0);8u(H)
343 13(14)Z;15(=0,OH);17(=0);3u(OH);8u(OH)
344 13(14)Z;15(=O,OH);17(=0,OH);8~(H)
345 13(14)E;15(=0,OH);17(=0,OH);8~(H)
346 13(14)Z;15(=0,OH);3(=0);8(-0-)17
347 13(14)E;8~(-0-)17;15(Obern)
348 13(14)E;8(OH);15(OH)
349 13(14)E;15(=0);8(OH)
350 13(14)Z;15(=0);8(OH)
351 7(8);13(14)E;6~(OH);15(OH)
352 7(8);13(14)Z;6(=O);15(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
353 7(8);13(14)E;11(OH);3a(OAc);15(OAc)
354 7(8);13(14)E;15(=O,OH)
355 7(8);13(14)E;15(=O,OH);2~(OAng)
356 6(7);8(17);15(=O,OH)
357 8(17);2a(OH);15(OH)
358 13(S);8(17);15(=O,OH);2a(Oi-Val)
857 8(17);15(=O,OH);2a(OH)
858 8(17);15(=O,OH);2a(OAng)
859 8(17);15(=O,OH);2a(OTig)
860 8(17);15(=O,OH);2a(02-Mebut)
861 8(17);15(=O,OH);2(=O)
862 15(=O,OH);2a(OAng);8~(-O-)17
863 15(=O,OH);2a(02-Mebut);8~(-O-)17
359 8(17);2(=O);15(OH)
360 7(8);15(=O,OH);17(OMe)
361 7(8);15(=O,OH);2~(OAng)
362 7(8);13(14)Z;15(OH);16(OH);17(OH)
363 7(8);13(14)Z;15(OAc);16(OAc)
364 7(8);13(14)Z;15(OAc);16(OAc);17(OAc)
365 6(7);8(17);13(14)E;15(=O,OH);16(OH)
366 7(8);13(14)Z;15(=O,OH);16(OH)
367 7(8);13(14)Z;15(=O,OH);16(OH);17(OH)
368 7(8);13(14)Z;15(=O,OH);16(=O);12(OH)
369 7(8);13(14)Z;15(=O,OH);17(=O);16(OH)
370 7(8);13(14)Z;15(=O,OH);17(OH);16(OAc)
371 7(8);13(14)E;15(=O,OH);17(=O);16(OAc)
372 7(8);13(14)E;15(=O,OH);17(=O);6a(OH);16(OAc)
373 7(8);13(14)E;15(=O,OH);17(=O);6~(OH);16(OAc)
374 7(8);13(14)Z;15(=O,OH);6(=O);16(OAc)
375 7(8);13(14)Z;15(=O,OH);6(=O);16(=O)
TABLE 2. (contd.)
Compound:
No. Substituents
376 7(8);13(14)E;15(=0,OH);6(=0);16(OH)
377 7(8);13(14)E;15(=0,OH);6(=0);16(OAc)
378 7(8);13(14)E;15(=0,OH);6(=0);16(OMe)
379 6(7);13(14)E;15(=0,OH);8a(OH);16(OH)
380 6(7);13(14)E;15(=0,OH);17(=0);16(OAc);8a(H)
381 6(7);13(14)E;15(=0,OH);17(=0,OH);16(OAc);8a(H)
382 8(17);13(14)Z;7~(OH);15(OH);16(OH)
383 8(17);15(=0,OH);16(=0)
384 6(7) ;8(17) ;13(14) ;15(=0) ;15(-0-)16
385 8(17);13(14);15(=0);19(OH);15(-0-)16
386 7(8);13(14);15(=0);15(-0-)16
387 7(8);13(14);15(=0);12(OH);15(-0-)16
388 7(8);13(14);15(=0);16a(OH);15(-0-)16
389 7(8);13(14);15(=0);16~(OH);15(-0-)16
390 7(8);13(14);15(=0);12(OH);16(OH);15(-0-)16
391 7(8);13(14);15(=0);12(OH);16a(OH);15(-0-)16
392 7(8);13(14);15(=0);12(OH);16~(OH);15(-0-)16
393 7(8);13(14);6(=0);15(=0);15(-0-)16
394 7(8);13(14);6(=0);15(=0);16(OH);15(-0-)16
395 7(8);13(14);15(=0);17(=0);16a(OH);15(-0-)16
396 7(8);13(14);15(=0);17(=0);16~(OH);15(-0-)16
397 8(17);13(14);16(=0);7~(OH);15(-0-)16
843 8(17);13(14);18(=0,OH);16(=0);15(-0-)16
398 7(8);13(14);16(=0);15(-0-)16
399 7(8);13(14);16(=0);12(OH);15~(OH);15(-0-)16
400 7(8);13(14);16(=0);12(OH);15a(OH);15(-0-)16
401 8(17);13(16);14(15);7~(OH);15(-0-)16
402 8(17);13(16);14(15);7~(OAc);15(-0-)16
403 8(17);13(16);14(15);19(OH);15(-0-)16
404 8(17);13(16);14(15);6~(OH);19(OH);15(-0-)16
TABLE 2. (contd.)
Compound:
No. Substituents
839 8(17);13(16);14(15);19(=O,OH);15(-O-)16
840 8(17);13(16);14(15);19(=O,OH);3a(OH);15(-O-)16
841 8(17);13(16);14(15);18(OH);19(OH);15(-O-)16
842 8(17);13(16);14(15);3a(OH);18(OH);15(-O-)16
974 8(17);13(16);14(15);18(OH);3a(OAng);15(-O-)16
975 8(17);13(16);14(15);3a(OH);18(OAng);15(-O-)16
830 8(17);13(16);14(15);18(=O,OH);15(-O-)16
831 8(17);13(16);14(15);18(=O,OH);3a(OH);15(-O-)16
832 8(17);13(16);14(15);18(=O,OH);3a(OAng);15(-O-)16
833 8(17);13(16);14(15);18(=O,OH);3a(02-Mebut);15(-O-)16
834 8(17);13(16);14(15);18(=O,OH);3a(Oi-But);15(-O-)16
835 8(17);13(16);14(15);18(=O,OH);19(OH);15(-O-)16
836 13(16);14(15);18(=O,OH);8a(-O-)17;15(-O-)16
837 13(16);14(15);18(=O,OH);8~(-O-)17;15(-O-)16
838 13(16);14(15);18(=O,OH);17(=O);8~(H);15(-O-)16
405 1(2);8(17);13(16);14(15);18(=O,OH);15(-O-)16
406 8(17);13(16);14(15);2(=O);12(OH);15(-O-)16
407 8(17);13(16);14(15);2(=0);12(=0);15(-0-)16
408 8(17);13(16);14(15);18(OH);7~(OAc);15(-O-)16
409 8(17);13(16);14(15);7~(OAc);18(OAc);15(-0-)16
410 8(17);13(16);14(15);18(=0);7~(OH);15(-0-)16
411 8(17);13(16);14(15);18(=0);7~(OAc);15(-O-)16
412 8(17);13(16);14(15);2(=O);12(=0);3a(OH);15(-0-)16
413 8(17);13(16);14(15);2(=O);3a(OH);12(OH);15(-0-)16
414 7(8);13(16);14(15);17(OH);15(-0-)16
415 7(8);13(16);14(15);18(=O,OH);15(-O-)16
416 13(16);14(15);8(OH);3a(OAng);15(-O-)16
417 8(17);13(14);2(=O);12(=O);15a(OH);15(-O-)16
418 8(17);13(14);2(=O);12(=O);15~(OH);15(-O-)16
421 8(17);12(13);14(15);6~(OH);12(-0-)15
TABLE 2. (contd.)
Compound:
No. Substituents
422 8(17);12(13)Z;14(15)
423 8(17);12(13)Z;14(15);18(=O)
424 8(17);12(13)Z;14(15);18(=O,OH)
425 8(17);12(13)E;14(15);18(=O,OH)
426 8(17);12(13)Z;14(15);18(=O,OH);2a(OH)
427 8(17);12(13)Z;14(15);18(=O,OH);2(=O)
428 12(13)Z;14(15);6~(OH);7a(OH);8(OH)
429 12(13)Z;14(15);7a(OH);8(OH);6~(OAc)
808 12(13)Z;14(15);8~(OH);6~(OAng);7a(OAc)
430 8(17);12(13)E;14(15)
431 8(17);12(13)E;14(15);19(OH)
432 8(17);12(13)E;14(15);3a(OH);19(OH)
433 8(17);12(13)E;14(15);18(OH)
434 8(17);12(13)E;14(15);18(OH);19(OH)
435 8(17);12(13)E;14(15);18(=O,OH);1~(OAc)
436 12(13)E;14(15);3~(OH);8~(OH)
809 12(13)E;14(15);6~(OH);7a(OH);8~(OH)
810 12(13)E;14(15);7a(OH);8~(OH);6~(OAc)
811 12(13)E;14(15);8~(OH);6~(OAng);7a(OAc)
441 13(16);14(15);8a(OH)
442 8(17);14(15);13a(OH)
443 8(17);14(15);2~(OH);13a(OH)
444 8(17);14(15);2a(OH);13a(OH)
445 8(17);14(15);13a(OH);2~(OSucc)
446 8(17);14(15);2(=O);13a(OH)
447 7(8);14(15);13(OH)
448 7(8);14(15);3(OH);13(OH)
449 7(8);14(15);3(=O);13(OH)
450 14(15);8a(OH);13a(OH)
460 13(14)Z;15(=O,OH);6(=O);16(=O);8(-O-)12
TABLE 2. (contd.)
Compound:
No. Substituents
461 13(S);1(OH);6~(OH);7~(-O-)8~;15(OSen);5~(H);9~(-O-)13
1012 7(8);13(14)E;2~(OH);15(OAc);18(OAC)
1013 7(8);13(14)E;2~(OH);15(OH);18(OAc)
1014 8(17);13(14)E;15(OH);3a(OAc);18(OTig)
1015 12(13)E;14(15);8~(OH);18(OH)
1016 8(9);14(15);7(=O);13~(OH);18(OH)
1017 14(15);7(=O);18(OH);9~(-O-)13~;8~(H)
1018 14(15);7(=O);18(=O);9~(-O-)13~;8~(H)
1019 14(15);18(=O,OH);7(=O);9~(-O-)13~;8~(H)
1037 8(17);13(16);14(15);18(OH);3a(OAng);15(-O-)16
1038 8(17);13(16);14(15);2~(OH);18(OH);3a(OAng);15(-O-)16
1039 8(17);13(14)Z;2~(OH);15(OH);16(OH);18(OH);3a(OAng)
1040 8(17);13(14)E;15(=O,OH)
1041 8(17);13(14)E;15(=O,OH);18(OH)
1042 7(8);13(14)E;15(=O,OH);18(=O);6~(OH)
1043 7(8);13(14)E;15(=O,OH);18(=O,OH);6~(O-i-Va1)
1044 13(14)E;15(=O,OH);5~(-O-O-)8~
1045 7(8);13(14)E;15(=O,OH);6~(OH);18(OH)
1046 7(8);15(=O,OH);17(OH)
1047 7(8);15(=O,OH);17(OAc)
1048 7(8);15(=O,OH);17(=O)
1049 7(8);15(=O,OH);2a(OH);17(OH)
1050 7(8);15(=O,OH);2a(OH);17(OAc)
1051 7(8);15(=O,OH);17(=O);2a(OH)
1052 7(8);15(=O,OH);17(=O,OH)
1053 7(8);15(=O,OH);19(OH);i7(OAC)
1164 8(17);13(14)E;15(=O,OH);18(=O,OH)
1173 8(17);19(=O,OH);15(OH)
1174 13(14)E;2~(OH);8~(OH);15(OH)
1175 7(8);15(=O,OH);3a(OH);17(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
1176 7(8);15(=O,OH);3a(OH);17(OAc)
1177 7(8);15(=O,OH);17(=O);3a(OH)
1178 7(8);15(=O,OH);3a(OH);17(OMe)
1179 7(8);15(=O,OH);2(OH);17(OMe)
1180 7(8);13(14)Z;15(=O,OH);16(OH);17(OMe)
1181 8(17);13(14)Z;15(=O);18(OH);2~(OH);15(-O-)16
1182 8(17);13(14)Z;15(=O);18(OH);3a(OAng);15(-O-)16
1183 8(17);13(14)Z;15(=O);18(OGlu);3a(OAng);15(-O-)16
1184 8(17);13(14)Z;15(=O);2~(OH);18(OH);3a(OAng);15(-O-)16
1185 8(17);12(13)E;14(15);18(OAc);19(OAc)
1186 8(17);12(13)E;3a(OH);14(OH);15(OH)
1188 7(8);13(16);14(15);2~(OH);3a(OH);15(-O-)16
1189 8(17);13(14)E;15(=O,OH);3a(OH);18(OH)
1190 8(17);13(14)E;15(=O,OH);18(OH);3a(OAng)
1191 8(17);13(14)Z;15(=O,OH);2~(OH);16(OH);18(OH);3a(OAng)
1192 7(8);13(14)E;2~(OH);15(OH);3a(OAng)
1193 7(8);13(14)E;2~(OH);3~(OH);15(OH)
1194 6(7);8(17);13(14)E;15(=O,OH)
1195 6(7);8(17);13(14)E;15(=O,OH);18(OH)
1196 7(8);15(=O,OH);2~(OH);3~(OH)
1197 7(8);2~(OH);3~(OH);15(OH)
1. 1.
1165 7(8);13(14)E;15(OH);3a(OAng);2'~(OH);3'a(OH);4'a(OH)
1166 7(8);13(14)E;15(OH);3a(OAng);2'~(OH);3'a(OH);4'a(OAc)
1167 7(8);13(14)E;15(OH);3a(OAng);2'~(OH);3'a(OAc);4'a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
1168 7(8);13(14)Z;15(OH);16(OH);3a(OAng);2'~(OH);
3'a(OH);4'a(OAc)
1169 7(8);13(16);14(OH);15(OH);3a(OAng);2'~(OH);
3 'a(OH) ; 4' a(OAc)
12 14
4'
~,
3'1 2' 3
CH 3
" " 11
1170 7(8);13(14)E;15(OH);3a(OAng);2'~(OH);3'a(OH);4'~(OAc)
12 14
J' 2' °
18 19
1171 7(8);13(14)E;15(OH);3a(OAng);2'~(OH);3'a(OH);4'B(OH)
12 14
20
15
°
,
5
7
'1/0-........,.
1 ~ 4'
8
J
18 19
1172 13(14)E;15(OH);2'a(OH);3'~(OH);4'a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
18
15
3
18
437 8(17);14(15);18(=O,OH)
t.
1IS
18 18
438 8(17);14(15);18(=O,OH)
18 18
439 8(17);14(15);18(=O,OH)
TABLE 2. (contd.)
Compound:
No. Substituents
HI 18
440 8(17);14(15);18(=O,OH)
39. ent-Labdane-19,6-Lactone
12 14
20
15
II
o
CO H
18
::1
462 7(8);15(=O,OH)
40. ent-Labdane-8,13-Epoxide-15,16-Hemiacetal
0
)15
111
1J
11111
o 14
2
18 18
463 14(OH);16~(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
464 14(OH);16~(OAc)
97. ~-Labdane Dimer
12 14
15
18 19
11' 20
H 19'
IS'
419 8(17) ;13(16) ;14(15) ;7a(H) ;8' (17') ;15' (=0) ;16'a(H)
420 8(17) ;13(16) ;14(15) ;7a(H) ;8' (17') ;15' (=0) ;16'~(H)
98. ent-Manoyl Oxide, 13-Epi-

16
18 19
451 14(15)
TABLE 2. (contd.)
Compound:
No. Substituents
452 14(15);3a(OH)
453 14(15);3(=0)
454 14(15);2(=0)
455 14(15);19(OH)
456 14(15);2(=0);19(OH)
457 14(-0-)15;16(OAc)
1198 14(15);3a(OAc)
1199 14(15);3a(OH);19(OCinn)
1200 14(15);3a(OH);19(OH)
99. ent-Manoyl Oxide

18
12
14
2 18
18 11
458 14(15)
459 14(15);3~(OH)

12 14
18 11
TABLE 2. (contd.)
Compound:
No. Substituents
465 6(7);13(14)E;15(=0,OH);8~(OCHO);16(OAc)
466 6(7);13(14)E;15(=0,OH);8(=0);16(OAC)
467 13(14)Z;15(=0,OH);8(=0);3a(OH)
468 13(14)Z;15(=0,OH);3(=0);8(=0)
1201 13(14)Z;15(=0,OH);8(=0)
1202 13(14)Z;15(=0,OH);3(=0);8(=0)
12 14
469 8(17);12(13)E;19(=0,OH);14(=0)
12
16
18 19
470 8(17);13(=0)
TABLE 2. (contd.)
Compound:
No. Substituents
12
4
<t-~
J'I 2' 0
CH J
,
8
18 19
1203 7(8);13(=0);3a(OAng);21~(OH);3Ia(OH);4'a(OAc)
12
20
"
2
" 11
471 7(8);12(=0)
472 7(8);12(=0,OH);17(OH)
45. ent-Labdane, 7,a-Seco-

12 14
18 19
473 12(13)E;14(15);7(=0,OH);8(=0)
TABLE 2. (contd.)
Compound:
No. Substituents
11
20
4
-
H ,
"
828 7(=O);2a(OH);3a(OH);19(OH);8a(H)
829 7(=O);12(=O);2a(OH);3a(OH);19(OH);8a(H)
1205 7(=O);3a(OH);19(OH);2a(OAc);8a(H)
1206 7(=O);2a(OH);3a(OH);19(OH);8a(H)
1207 7(=O);12(=O);3a(OH);19(OH);2a(OAc);8a(H)
12 14
15
11 11
1059 5(6);13(14)E;15(=O,OH);18(OH);10~(H)
1208 5(6);13(14)E;15(=O,OH);18(OH);10~(H)
1209 1(10);13(14)E;2(=O);15(OH);5~(H)
1210 1(10);13(14)E;2a(OH);15(OH);5~(H)
1211 1(10);14(15) ;19(=O,OH);13(OH);5~(H)

TABLE 2. (contd.)
Compound:
No. Substituents
15
Co
1.
~
H 13
16
0
2 11111
17
3
7
1212 3a(OH);5a(OH)
1213 5(6);3a(OH)
1214 3a(OH);5~(-0-)10~
102. ent-Friedolabdane, 3,4-Seco-
18
1215 3(=0)
1216 3(=0,OH)
TABLE 2. (contd.)
Compound:
No. Substituents
1217 3(=O,OH);19(OH)
1218 3(=O,OMe);19(OH)
14 IS
Ie Ie
1219 4(18)
14
Ie
,.
1220 4(5);3(=O,OH)
TABLE 2. (contd.)
Compound:
No. Substituents
103. ent-Friedolabdane, Rearranged 3,4-Seco-
f5
f4
1221
12 14
115
236 4(18);13(14)E;15(OH)
248 1(2);3(4);13(16);14(15);18(=O,OH);15(-O-)16
249 3(4);13(16);14(15);18(=O,OH);15(-O-)16
TABLE 2. (contd.)
Compound:
No. Substituents
250 1(2) ;3(4) ;13(16) ;14(15) ;18(=0,OH) ;15(-0-)16
251 1(2);3(4);13(16);14(15);18(=0,OMe);15(-0-)16
245 3(4);13(16);14(15);18(=0,OH);15(-0-)16
475 3(4);13(14)E;15(OH)
476 3(4);13(14)E;15(OH);17(OH)
477 13(14)E;3~(-0-)4~;2a(OH);15(OAc)
478 13(14)Z;3~(-0-)4~;2a(OH);16(OH);15(OAc)
1010 3(4);13(14)E;17(OH);15(OArac)
1011 3(4);13(14)E;17(OH);15(OBehen)
479 3(4);14(15);13(OH)
480 3(4);14(15);13(OH);6~(OAng)
481 3(4);15(OH);17(OH)
482 3(4);17(OH);15(OArac)
483 3(4);17(OH);15(OBehen)
484 3(4);15(OH);18(OSucc)
485 3a(-0-)4a;2a(OH);15(OH)
486 3(4);17(=0);15(OH)
487 3(4);18(=0);18(-0-)6a;15(OH);17(OAc)
488 3(4);6a(OH);15(OH);18(OH);17(OAc)
489 3(4);6a(OH);15(OH);18(OH);17(OPhe-Ac)
490 3(4);18(=O);6a(OH);15(OH);17(OPhe-Ac)
491 3(4);18(=0);6a(OH);15(OH);17(OAc)
492 3 ( 4 ) ; 15 ( =0) ; 17 ( OH )
493 3(4);13(14)Z;15(=O,OH)
494 3(4);13(14)Z;15(=0,OH);2~(OAc)
495 3(4);13(14)E;15(=0,OMe)
496 3(4);13(14)E;15(=O,OMe);6~(OAc)
497 3(4);13(14)E;15(=O,OMe);6~(OAng)
498 3(4);13(14)E;15(=0,OH);6a(OAng)
499 3(4);13(14)E;15(=O,OH);6a(OTig)
TABLE 2. (contd.)
Compound:
No. Substituents
500 3(4);13(14)E;15(=0,OH);7a(OAc)
962 13(14)Z;15(=0,OH);2a(OH);3a(OH);4~(OH)
501 3(4);13(14)E;15(=0,OH);6a(OH);18(OH);17(OAc)
502 3(4);13(14)E;15(=0,OH);6a(OH);18(OH);17(OPhe-Ac)
503 3(4);15(=0,OH)
504 3(4);15(=0,OH);18(OAc)
961 3(4);13(14)E;15(=0,OH);2(=0)
505 13(S);3(4);15(=0,OH);18(=0,OH)
506 15(=0,OH);2(=0);3~(-0-)4~
507 3(4);13(16);14(15);15(-0-)16
508 3(4);13(16);14(15);18(OMal);15(-0-)16
509 3(4);13(16);14(15);7a(OH);18(OH);15(-0-)16
846 3(4);13(16);14(15);18(OH);19(OH);15(-0-)16
510 3(4);13(16);14(15);19(OAc);18(OMal);15(-0-)16
967 3(4);13(16);14(15);17(=0);15(-0-)16
511 3(4);13(16);14(15);18(=0,OH);15(-0-)16
953 3(4);13(16);14(15);18(=0,OH);12a(02-Mebut);15(-0-)16
512 1(2);3(4);13(16);14(15);18(=0,OH);15(-0-)16
911 1(2);3(4);13(16);14(15);18(=0,OH);19(OAc);15(-0-)16
513 3(4);13(16);14(15);18(=0,OH);2a(OH);15(-0-)16
514 7(8);13(16);14(15);3a(OH);18(Oi-Val);4~(H);15(-0-)16
515 7(8);13(16);14(15);3a(OH);18(02-Mebut);4~(H);15(-0-)16
516 7(8);13(16);14(15);3a(OH);18(OAng);4~(H);15(-0-)16
518 3(4);13(16);14(15);18(=0,OH);19(OH);15(-0-)16
519 3(4);13(16);14(15);18(=O,OH);2~(OH);19(OH);15(-0-)16
900 3(4);13(16);14(15);18(=0,OH);19(OAc);15(-0-)16
901 3(4);13(16);14(15);18(=O,OH);19(OMe);15(-0-)16
902 3(4);13(16);14(15);18(=0,OH);19(OAng);15(-0-)16
903 3(4);13(16);14(15);18(=0,OH);19(Oi-Va1);15(-0-)16
904 3(4);13(16);14(15);18(=0,OH);19(=0);15(-0-)16
TABLE 2. (contd.)
Compound:
No. Substituents
524 3(4);13(16);14(15);20(=0,OH);15(-0-)16
520 3(4);13(16);14(15);18(=0);15(-0-)16;18(-0-)19
950 3(4);13(16);14(15);18(=0);12a(OH);15(-0-)16;18(-0-)19
951 3(4);13(16);14(15);18(=0);7a(OH);12a(OH);
15(-0-)16;18(-0-)19
521 3(4);13(16);14(15);18(=0);1a(OH);15(-0-)16;18(-0-)19
522 3(4);15(=0,OH);18(=0);17(OPhe-Ac);6a(-0-)18
523 3(4);13(16);14(15);7(=0);18(=0);6a(-0-)18;15(-0-)16
534 3(4);13(14)Z;15(=0);17(OH)
535 3(4);13(14)E;15(=0);17(OH)
536 3(4);13(14)Z;17(=0,OH);15(=0)
537 3(4);13(14)E;l7(=0,OH);15(=0)
865 13(14)E;3(4);15(=0,OH);16(OH)
962 13(14)E;3(4);15(=0,OH);6a(OAc)
538 3 ( 4 ) ; 13 ( 14 ) Z ; 15 (=0, OH) ; 16 (OH) ; 18 (OH)
539 3(4);13(14)Z;15(=0,OH);18(OH);16(OAc)
540 3(4);13(14)Z;15(=0,OH);18(=0);16(OH)
541 3(4);13(14)Z;15(=0,OH);18(=0);16(OAc)
542 3(4);15(=0,OH);16(=0)
543 3(4);13(14);15(=0);15(-0-)16
544 3(4);13(14);15(=0);2a(OH);15(-0-)16
864 3(4);13(14);15(=0);16(OH);15(-0-)16
550 3(4) ;13(14) ;15(=0) ;18(OH) ;15(-0-)16
558 3(4);13(14);18(=0,OH);15(=0);15(-0-)16
909 3(4);13(14);18(=0,OH);15(=0);16a(OAc);19(OAc);
15(-0-)16
910 3(4) ;13(14) ;18(=O,OH) ;15(=0) ;1613(OAC) ;19(OAc);
15( -0-)16
559 3(4);13(14);15(=0);18(=0);7a(OH);15(-0-)16;18(-0-)19
560 3(4);13(14);15(=O);18(=0);12(OH);15(-0-)16;18(-0-)19
561 3(4);7(=0);15(=0);18(=0);15(-0-)16;18(-0-)19
TABLE 2. (contd.)
Compound:
No. Substituents
562 3(4);15(=0);18(=0);7a(OH);15(-0-)16;18(-0-)19
563 3(4);15(=0);18(=0);15(-0-)16;18(-0-)19
564 3(4);15(=0);15(-0-)16
565 3(4);15(=0);16(OH);15(-0-)16
963 3(4);15(=0);18(OAc);16(OMe);15(-0-)16
566 3(4);13(14);16(=0);20(=0);15(-0-)16
905 3(4);13(14);18(=0,OH);16(=0);15a(OH);19(OH);15(-0-)16
906 3(4);13(14);18(=0,OH);16(=0);15~(OH);19(OH);15(-0-)16
907 3(4);18(=0,OH);16(=0);19(OH);14a(-0-)15a;15(-0-)16
908 3(4);18(=0,OH);16(=0);19(OH);14~(-0-)15~;15(-0-)16
567 3(4);13(14);16(=0);2~(OH);15(-0-)16
568 3(4);13(14);2(=0);16(=0);15(-0-)16
569 3(4);15(OH);18(OMal);15(-0-)16
1027 3(4);13(14)Z;15(=0,OH);6a(0-i-But);7~(OAC)
1028 3(4);13(14)Z;15(=0,OH);6a(OAng);7~(OAc)
1029 3(4);13(14)Z;15(=0,OH);6a(OAc);7~(OAc)
1030 3(4);13(14)E;15(=O,OH);2(=O);6a(OH);7~(OH)
1031 3(4);15(=0,OH);6a(O-i-But);7~(OAng)
1033 3(4);13(16);14(15);18(=O,OH);19(OH);15(-O-)16;8~(H)
1034 3(4);13(16);14(15);18(=0,OH);2~(OH);19(OH);
15(-O-)l6;8~(H)
1070 1(2);3(4);13(16);14(15);18(=0,OH);19(OH);15(-0-)16
1071 13(16) ;14(15) ;20(=0,OH) ;3a(-O-)4a;15(-0-)l6;8~(H)
1075 13(14)Z;15(=0);3a(-0-)4a;8~(H)
1076 13(16);14(15);3a(-0-)4a;15(-0-)16;8~(H)
1077 13(14)E;15(=0);3a(-O-)4a;8~(H)
1078 13(14)Z;3(=0);15(=0);4~(H);8~(H)
1079 13(14)E;3(=0) ;15(=0) ;4~(H) ;8~(H)
1080 13(14);15(=0);3a(-0-)4a;15(-0-)16;8~(H)
1081 13(14);3(=O);15(=O);15(-O-)16;4~(H);8~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
1082 13(14);15(=O);3a(OH);4~(OH);15(-O-)16;8~(H)
1222 3(4);13(14)Z;15(OH);16(OH);18(OH)
1223 3(4);13(14)E;18(=O,OH);6a(OH);15(OH)
12Z4 3(4);13(14)E;17(=O,OH);15(OH)
1225 3(4);13(14)Z;17(=O,OH);16(OH);15(OAc)
1227 3(4);13(14)E;15(OAc);18(OAc)
1228 13(14)Z;16(OH);3a(OAc);15(OAc);3~(-O-)4~
1229 3(4);15(OAc);18(OAc)
1230 3(4);15(OAc);16(OAc);18(OAc)
1231 3(4);13(16);14(15);18(OH);19(OMal);15(-O-)16
1232 3(4);13(16);14(15);18(OH);15(-O-)16
1233 3(4);13(16);14(15);18(OAc);19(OAc);15(-O-)16
1234 3(4);13(16);14(15);18(=O);15(-O-)16;18(-O-)6a
1235 3(4);13(16);14(15);18(=O);7a(OH);15(-O-)16;18(-O-)6a
1236 3(4);13(14)Z;15(=O);16(OMe);18(OAc);15(-O-)16
1237 3(4);13(14)Z;15(=O);18(=O);2(OH);15(-O-)16;18(-O-)19
1238 3(4);13(14)Z;15(=O);18(=O);2(OAc);15(-O-)16;18(-O-)19
1239 3(4);18(OAc);15(OMe);15(-O-)16
1240 3(4),13(14)Z;16(=O);18(OAc);15(-O-)16
1241 3(4);18(OH);15(OMe);15(-O-)16
1242 3(4);18(OH);19(OH);15(OMe);15(-O-)16
1243 3(4);18(OAc);19(OAc);15(OMe);15(-O-)16
12 14
II
1226 3(4);13(14)E
TABLE 2. (contd.)
Compound:
No. Substituents
12 I.
111
\I
570 3(4);13(14)Z;15(=0,OH);20(OH)
,. HI
525 3(4);8(17);7(=O);12a(H)
526 3(4);7(8)i17(=O);7(OH);12a(H)
527 3(4);17(=O);8~(H);12~(H)
528 3(4);17(-0-)20;8~(H);12~(H);17~(H)
969 3(4) ;8(17) ;7(=0) ;12~(H)
970 3(4)i7(=O)i8~(H);12~(H)
971 1(=0);17(=O)i6a(OAng)i8a(H);12a(H)
972 3(4);7(8);17(=O);6~(OH);12~(H)
973 2(3);17(=0);8a(H);12a(H)
1069 3(4);17(=O);la(OH);12~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
1257 3(4);17(=O);1a(OAc);8~(H);12~(H)
1258 3(4);17(=O);7a(OH);8~(H);12~(H)
12
16
11 0
H 20L
\I\\I~O
2
10 9 11111
8
5 17
.3 4
,- 7
19 ---;.
/ 6
0
0'
529 3(4);12~(H)
968 3(4);2a(OAng);12~(H)
530 3(4);7~(OAng);12~(H)
531 2a(OAng);3a(OSen);12~(H)
532 3(4);2a(OSen);12~(H)
533 3(4);2a(02-Mebut);12~(H)
12
14 14' 12'
1;~~.o\;)~'1~1'
11
r
I'
17 \ Ie' = H
"" ~o 0 -
2
, Ie .'
v
" ,10
J 7 ~ 4'
4
I
15'
1"
1244 3 ( 4 ) ; 3 ' ( 4 ' ) ; 18 ( OMa 1) ; 18 ' (OMa 1 )
TABLE 2. (contd.)
Compound:
No. Substituents
1245 3(4);3'(4' );18(OSucc);18'(OSucc)
47. Printziane
12 14
~'5
o
HO
o
571 5(10)
572 5(6);10~(H)
913 5a(OH);10~(H)
914 5a(OMe);10~(H)
915 1(2);5a(OH);10~(H)
12 ,.
::;;>---- 0 •
916 10r3(H)
76. Conyscabrane ,4
TABLE 2. (contd.)
Compound:
No. Substituents
917 5(6);18(=O,OH);la(H);10~(H)
919 18(=O,OH);5a(OH);la(H);10~(H)
14
15
5
19
6
918 5(6);18(=O,OH);1~(H);10~(H)
920 18(=O,OH);5a(OH);1~(H);10~(H)
48. ent-Clerodane, 5,lO-Seco-
12 14
15
573 1(2);3(4);13(16);14(15);18(=O,OH)
912 1(2);3(4);13(16);14(15);18(=O,OH);19(OAc)Z
985 1(2);3(4);13(14);18(=O,OH);16(=O)
986 1(2);3(4);13(14);18(=O,OH);15(=O)
987 1(2);3(4);18(=O,OH);16(=O);14(-O-)15;
952 1(2) ;3(4) ;13(16) ;14(15) ;18(=O,OH) ; 12a(02-Mebut)
TABLE 2. (contd.)
Compound:
No. Substituents
96. trans-ent-Clerodane, 17-Nor-
15
8
19
18
1061 3(4)i13(16)i14(15)i7(=O)i18(=O)i12(OH)i18(-O-)19
49. trans-ent-Clerodane, 13,14,15,16-Tetra-Nor-
12
H
2 \\\\' 17
10 9
8
J 5
4 7
--
6
18 19
574 3(4)i12(OH)i18(OH)
575 3(4)i12(=O,OH)i18(OH)
1032 3(4)i12(=O,OH)i6a(OH)i7~(OH)
1093 1(2)i3(4)i12(=O,OH)i18(=O,OH)i19(OH)i8~(H)
Undetermined
12 14
15
J
TABLE 2. (contd.)
Compound:
No. Substituents
237 8(S);3(4);13(14)E;15(OH)
12 14
11 lJ
20
-- 9 15
17
2 --- 18
10
H 8
5
7
6
578 3(4);13(16);14(15);15(-0-)16
579 3(4);13(16);14(15);18(OH);15(-0-)16
580 3(4);13(16);14(15);18(OAc);15(-0-)16
576 3(4);13(14);15(=O,OH);18(=O,OH)
577 3(4);13(4);15(=0,OH);18(=0,OMe)
581 3(4);13(16);14(15);6a(OH);18(OH);15(-0-)16
582 3(4);13(16);14(15);6a(OH);18(OAC);15(-0-)16
583 3(4);13(16);14(15);18(=0);15(-0-)16;6a(-0-)18
584 3(4);15(=0);18(=0);15(-0-)16;6a(-0-)18
585 3(4);15(=0);18(=0);2~(OH);15(-0-)16;6a(-0-)18
1055 3(4);13(14)E;15(=0,OH);18(OAC)
1056 3(4);13(14)E;15(=0,OH);18(OH)
1057 3(4);15(=0,OH);18(OH)
1058 3(4);15(=O,OH);19(OH)
1246 13(16);14(15);20(=0);3~(-0-)4~;20(-0-)12;
15(-0-)16;12a(H)
TABLE 2. (contd.)
Compound:
No. Substituents
82. Solidagonane 12
H
o
7
H
19
18
960
VI. ent-Tricarbocyc1ics and Derivatives

51. ent-Labdane, Cyc1opropy1-
12 14
11 13
20
-- 9
17
15
2 --- 18
10
H 8
5
7
6
586 14(15);8a(OH);13a(OH)
77. Gutierreziane
12 14
11
20 ~ 15
---
2 --
10 8 'I'I/
5
3 4 17
7
H 8
18 19
845 17(=O);18(=O,OH)
TABLE 2. (contd.)
Compound:
No. Substituents
52. ent-Pimarane
17
20
=
--
2 -
10 8
J .. ~
7
.,.,
., H
., 8
18 Ii
587 15(16);8~(OH);9~(H)
588 15(16);8~(OH);11a(OH);12~(OAc);9~(H)
589 8(14);2~(OH);15(OH);16(OH);19(OH);9~(H)
590 8(14);15(16);19(=O,OH);9~(H)
820 7(8);15(16);19(=o,OH);9~(H)
821 8(9);15(16);19(=O,OH);7(=O)
823 9(11);19(=O,OH);12~(OAc)
591 8(14);3a(OH);15~(OH);16(OH);9~(H)
592 8(14);15~(OH);16(OH);3a(OGlu);9~(H)
593 8(14);15~(OH);16(OH);6~(OGlu);9~(H)
594 8(14);6~(OH);15~(OH);16(OH);9~(H)
595 8(14);2~(OH);15~(OH);16(OH);19(OH);9~(H)
944 8(14);6~(OH);15(OH);16(OH);18(OH);9~(H)
1247 8(14);15(16);3a(OH);19(OH);9~(H)
1248 8(14);15(16);3a(OH);18(OH);9~(H)
1249 8(9);15(16);7(=O);19(OH)
1250 9(11);15(16);19(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
HI
18 Ie
599 9(11);15(16);19(OH)
600 9(11);15(16);19(=O,OH)
1251 9(11);15(16);18(OH)
1252 9 (11) ; 15 (16) ; 18 (OMal)
1253 9(11);15(16);19(OMal)
1254 9(11);15(16);3a(OH);19(OH)
53. ent-Pimarane-8.15-Tetrahydrofuran
H~CH20H
12 .::
. -
17
18 19
596 3a(OH);12~(OH);16(OH)
598 3(=O);12~(OH);16(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
HOH2~H
12 ,:...
,
. --
11
20 17
9
2 14
824 9(11);19(=0,OH);12~(OAc)
597 3a(OH);12~(OH)
17
12
111 111
601 12(13);11(=0);15(-0-)16
602 12(13);11(=0);17(=0);15(-0-)16
603 12(13);11(=0);15(-0-)16;17(OAc)
604 12(13);11(=0);15(-0-)16;3a(OAng)
605 12(13);11(=0);14~(OH);15(-0-)16;17(OAc)
606 12(13);11(=0);15(-0-)16;3a(OAng);17(OAC)
607 12(13);11(=0);17(=0);8(-0-)9;15(-0-)16
608 12(13);11(=0);14~(OH);15~(OH);16(-0-)17;15a(H)
TABLE 2. (contd.)
Compound:
No. Substituents
85. Cleistanthane, Iso-
12 17
18 4
18
609 3(4);12(13);11(=O);15(-O-)16;17(OAc)
610 12(13);11(=O);3(-O-)4;15(-O-)16;17(OAc)
55. ent-Abietane
18
1 a llJ
611 8(14);3(=O);13(OH);5~(H)
612 8(14);3~(OH);13(OH);5~(H)
613 8(14);13a(OH);2~(OAc);5~(H)
614 7(8);13(14);5~(H)
615 7(8);13(14);5(OAc)
616 7(8);13(14);19(=O,OH);5~(H)
1054 7(8);13(14);19(O-Succ);5~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
14 15
,,'2~
(17 \16 H
2
18 19
617 7(8);13(14)E;15(=O,OH);6(=O);17(OH);16(OAc)
14 15
16
H
18 19
1100 13(14)Z;15(=O,OH);6(=O)
TABLE 2. (contd.)
Compound:
No. Substituents
83. Erythroxane
11
HI
976 3(4);15(16);18(=O,OH)
VII. ent-Tetracarbocyclics and Derivatives

58. ent-Kaurane
12
11
20 17
---
2
7
6
18 19
618 16(17)
619 16 ( 17) ; 19 ( OH )
997 16a(OH)
620 16 ( 17) ; 19 ( OAe )
621 16(17);19(OMeform)
622 16(17);19(O-p-OH-H-Cinn)
TABLE 2. (contd.)
Compound:
No. Substituents
623 16(17);3a(OH);19(OH)
624 16(17);19(=0)
625 16(17);19(=0,OH)
626 16(17);18(OAc)
926 16(17);18(=0,OH)
939 16(17);18(=0.OH);19(OAng)
627 16(17);19(=0,OGly)
628 16(17);19(=0,OH);3a(OH)
629 16(17);19(=0,OH);3a(OAc)
630 16(17);19(=0,OH);3a(OAng)
631 16(17);19(=0,OH);3a(OTig}
632 16(17);19(=0,OH);3a(OCinn)
633 16(17);19(=0,OH);3a(OSen}
634 16(17);19(=0,OH);3a(Oi-Val)
635 16(17);18(=0)
636 16(17);19(=0,OH);9~(OH);13~(OH);15a(OAng)
637 16(17);19(=0,OH);11~(OH);15a(OH)
638 18(OH);16a(-0-)17
1000 16(17);19(=0,OH);7~(OH)
639 16(17);19(=O,OMe);9~(OH)
640 16(17);19(=0,OH);11~(OAc)
641 16(17);19(=0,OH);12a(OH)
642 16(17);19(=0,OH);12a(OAc) [=1108]
796 16(17);19(=0,OH);12~(OAc)
643 16(17);19(=0,OH);18(OAng)
644 16(17);19(=O,OH);18(OSen)
645 16(17);19(=O,OH);18(Oi-Val)
646 16(17);19(=O,OH);15a(OH)
647 16(17);19(=O,OH);15~(OH)
648 16(17);19(=0,OH);15a(OAc}
TABLE 2. (contd.)
Compound:
No. Substituents
649 16(17);19(=O,OH);15a(OAng)
1007 16(17);19(=O,OMe);9~(OH);15a(OAng)
650 16(17);19(=O,OH);15a(OTig)
651 16(17);19(=O,OH);15a(OSen)
652 16(17);19(=O,OH);15a(Oi-Val)
653 16(17);19(=O,OH);15a(02-Mac)
654 16(17);19(=O,OH);15a(Oi-But)
655 16(17);19(=O,OH);15a(OCinn)
656 16(17);19(=O,OH);15a(OEpoxyang)
657 16(17);19(=O,OH);15a(OBenz)
818 16(17);19(=O,OH);15a(02-Mebut-2,3-0H)
892 16(17);19(=O,OH);15a(02-Mebut)
658 16(17);19(=O,OH);15~(OAng)
659 16(17);19(=O,OH);15~(OTig)
660 16(17);19(=O,OH);15~(OSen)
661 16(17);19(=O,OMe);15a(OH)
662 16(17);19(=O,OH);9~(OH);3a(OAng)
663 16(17);19(=O,OH);9~(OH);3a(OCinn)
664 16(17);19(=O,OH);9~(OH);15a(OH)
665 16(17);19(=O,OH);9~(OH);15a(OAng)
666 16(17);19(=O,OH);9~(OH);15a(OTig)
667 16(17);19(=O,OH);9~(OH);15a(OAc)
668 16(17);19(=O,OH);9~(OH);15a(OSen)
669 16(17);19(=O,OH);9~(OH);15a(Oi-Val)
670 16(17);19(=O,OH);9~(OH);15a(OCinn)
819 16(17);19(=O,OH);9~(OH);15a(02-Mebut-3-0H)
671 16(17);19(=O,OH);11~(OH);15~(OH)
812 19(=O,OH);17(=O,OMe);16~(H)
672 16(17);19(=O,OH);11~(OH);15~(OAc)
673 16(17);19(=O,OH);11(=O);15~(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
674 16(17);19(=0,OH);15(=0);11~(OH)
675 16(17);19(=0,OH);3~(OH);9~(OH);15a(OAng)
869 16(17);19(=0,OH);9~(OH);11~(OH);15a(OAng)
676 16(17);19(=0,OH);3~(OH);9~(OH);15a(OSen)
677 16(17);19(=0,OH);3~(OH);9~(OH);15a(OTig)
690 9(11);16(17);19(=0,OH)
691 9(11);16(17);19(=0,OH);2~(OH)
692 9(11);16(17);19(=0,OH);3~(OH)
693 9(11);16(17);19(=0,OH);7~(OH)
694 9(11);16(17);19(=0,OH);12~(OH)
998 9(11);16(17);19(=0,OH);12~(OEt)
695 9(11);16(17);19(=0,OH);12(=0)
696 9(11);16(17);19(=0,OH);15a(OH)
697 15(16);17(OH)
698 15(16);17(OH);19(OH)
699 15(16);17(OH);19(Op-OH-H-Cinn)
946 15(16);19(=0)
700 15(16);19(=0,OH)
701 15(16);19(=0,OH);17(OH)
702 15(16);19(=0,OH);17(=0)
703 15(16);17(=0,OH);19(=0,OH)
704 9(11);15(16);19(=0,OH);3a(Oi-Val)
705 9(11);15(16);19(=0,OH);3a(Oi-But)
706 9(11);15(16);19(=0,OH);3a(OTig)
707 15(16);19(=0,OH);9~(OH);3a(Oi-Val)
708 15(16);19(=0,OH);9~(OH);3a(Oi-But)
733 16a(-0-)17
709 16a(-0-)17;3a(OAng)
734 19(OH);16a(-0-)17
710 16a(-0-)17;19(OAng)
711 19(=0);16a(-0-)17;3a(OAng)
TABLE 2. (contd.)
Compound:
No. Substituents
735 19(=O);16u(-O-)17
712 19(=O);16~(-O-)17
713 19(=O,OH);16u(-O-)17
714 19(=O,OH);16~(-O-)17
715 19(=O,OH);16(-O-)17;15u(OAng)
716 19(=O,OH);16(-O-)17;15u(OAc)
717 19(=O,OH);16(-O-)17;15~(OAng)
718 19(=O,OH);16(-O-)17;15~(OTig)
719 9(11);19(=O,OH);12~(OH);16u(-O-)17
720 16u(OH)
1001 16~(OH)
721 16u(OH);3~(OAc)
722 16u(OH);19(OAc)
723 19(=O,OH);16u(OH)
724 11(12);19(=O,OH);16u(OH)
725 16u(OH);17(OH)
726 16u(OH);17(OH);19(OH)
727 3(=O);16u(OH);17(OH)
851 16~(OH)
852 16~(OH);19(OH)
728 19(=O,OH);16u(OH);17(OH)
924 19(=O,OH);17(OH);16u(H)
925 17(=O,OH);19(=O,OH);16u(H)
822 19(=O,OH);16~(OH);17(OH)
729 17(=O);16~(H)
730 17(=O);19(OH);16~(H)
731 17(=O,OH);16~(H)
732 17(=O,OH);19(OH);16~(H)
736 17(=O,Me);19(OH);16~(H)
737 17(=O);19(=O);16~(H)
738 19(=O,OH);17(OH);16~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
739 9(11);19(=O,OH);16a(OH);17(OH)
989 17(=O,OH);19(=O);16~(H)
990 17(=O,OH);19(=O,OH);16~(H)
740 17(=O);19(Op-OH-H-Cinn)
741 19(=O,OH);17(Oi-But);16~(H)
742 19(=O,OH);17(ODodec);16~(H)
743 19(=O,OH);17(OTetradec);16~(H)
744 19(=0,OH);17(OHexadec);16~(H)
745 19(=0,OH);17(OOctadec);16~(H)
746 19(=0,OH);15a(-O-)16a;17(OH)
747 19(=O,OH);15(=O);II~(OH);16a(H)
748 19(=O,OH);15(=O);II~(OH);16a(H)
815 19(=O,OH);15(=O);IIS(OH);16a(H)
942 9(11);16(17);19(=0)
943 9(11);16(17);19(=O,OH);15a(OCinn)
1255 19(=0);16a(OH)
1256 9(11);19(=0,OH);16a(OH)
1260 16(17);19(=0,OH);II~(OH);12~(OH);15~(OH)
, 8'
2
3' 5'
,
8 9'
850
TABLE 2. (contd.)
Compound:
No. Substituents
945
II
678 Rl=R2=COOH;R3=OCOCH2CH(CH3)2;R4=R5=H03S0;15a(OH)
679 Rl=R2=COOH;R3=NHCOCH2CH(CH3)2;R4=CO(CH2)2C6H5;
R5=OH;13(OH);15(OH)
680 Rl=R2=COOH;R3=NHCOCH2CH(CH3)2;R4=CO(CH2)2C6H5;
R5=OL-Rha;13(OH);15(OH)
681 R1=H;R2=COOH;R3=OCOCH2CH(CH3) 2;R4=R5=H03S0; 15a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
12
20 17
J 15
895 16(17);15~(OH)
896 16(17);11~(OH);15~(OH)
897 16(17);15(=O);11~(OH)
898 16a(OH);17(OH)
899 16(17);15~(OGlu)
682 Rl=R2=H;R3=OH
683 Rl=~Glu;R2=H;R3=OH
TABLE 2. (contd.)
Compound:
No. Substituents
684 R1=H;R2=~G1u;R3=OH
685 R1=R2=~G1u;R3=OH
686 R1=~G1u;R2=R3=H
687 R1=R2=~G1u;R3=H
688 R1=~G1u[21-[11~G1u;R2=~G1u;R3=H
689 R1=~G1u[21-[11~G1u;R2=H;R3=OH
12
18
2
18 18
749 19(=O,OH);16(=O)
12
17
HI
752 16(17);4~(H);5~(H)
753 16 ( 17) ; 4 ~ (OH) ; 5 ~ (H)

754 4(5);6(7);16(17);3(=O);19(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
755 4(5);6(7);16(17);3(=0);19(=0)
756 4(5);6(7);16(17);3(=0);19(=0,OMe)
757 4(5);6(7);3(=0);16(-0-)17
758 16(17) ;19(=0,OH) ;213(OH) ;15u(OH) ;.413(H) ;513(H)

813 16(17);413(-0-)19;513(H)
12
17
18
750 16(17);4u(H)
751 16(17);4u(OH)
62. ent-Kaurane, 9,10-Seco-
12
17
18
19
759 1(10);16(17);19(=0,OH)
TABLE 2. (contd.)
Compound:
No. Substituents
12
17
~ 20 1 g 14
2 t 1~i ( 0 e \\\\\
J 4 e 7 1~
~ H
II! ~O
o HI
866 16(17);10~(OH);15a(OH)
867 16(17);10~(OH);15~(OH)
868 16(17);10~(OH);15~(OAc)
12
17
760 16(17);9(=0)
761 16(17);9a(OH)
762 16(17);9~(OH)
763 16(17);9{=O);15~{OH)
TABLE 2. (contd.)
Compound:
No. Substituents
17
16
18 1Q
764 15(16);3a(OH)
765 15(16);19(OH)
766 15(16);18(OH)
767 15(16);3a(OH);19(OH)
768 15(16);3a(OH);12~(OH)
769 15(16);19(OMal)
770 15 ( 16 ) ; 3a ( OH) ; 17 ( OH)
817 15(16);12~(OH);19(OH)
771 15(16);17(OH);19(OH)
772 15 ( 16 ) ; 18 ( OH) ; 19 ( OH )
774 15(16);19(=0,OH)
773 15(16);19(=0)
775 15(16);19(=0,OH);3a(OH)
776 15(16);19(=0,OH);3a(OTig)
777 9 ( 11 ) ; 15 ( 16 ) ; 19 ( =0 , OH )
778 9(11);15(16);19(=0,OH);3a(OTig)
779 18(OH);15~(-0-)16~
780 19(OH);15~(-0-)16~
TABLE 2. (contd.)
Compound:
No. Substituents
12 17
17
11
:i;
20 1J' III ,
l' 16
1.'
2
111111 I! ,
.:5
15
7
6'
18
,
18
781
93. ent-Stachane. 19-Nor-

17
11
20 18
HI
J
18
782 : J ( 16 I
65. Atisirane (Atisane)

12
17
.:5
H 6
18 19
TABLE 2. (contd.)
Compound:
No. Substituents
783 16(17);19(=O,OH);9~(H)
853 16a.(OH);9~(H)
854 16~(OH);9~(H)
816 13(14);3a.(OH);16~(OH);9~(H)
784 16(17);19(=O,OH);7a.(OH);9~(H)
785 16(17);19(=O,OH);11a.(OAc);9~(H)
786 16(17);19(=O,OH);13a.(OAng);9~(H)
787 16(17);19(=O,OH);13a.(Oi-Val);9~(H)
788 16(1?);19(=O,OH);13a.(Oi-But);9~(H)
789 9(11);16(17);19(=O,OH);7a.(OAc)
790 9(11);16(17);19(=O,OH);14~(OAc)
814 16(17);19(=O,OH);13(OH);9~(H)
66. Trachylobane
12
17
18 19
855 19(=O);9~H
791 19(=O,OH);9~(H)
825 19(=O,OH);15a.(OAc);9~(H)
826 19(=O,OH);15a.(OAng);9~(H)
827 19(=O,OH);15a.(Oi-Val);9~(H)
893 19(=O,OH);15a.(Oi-But);9~(H)
792 19(=O,OH);7a.(OH);9~(H)
793 19(=O,OH);11(=O);9~(H)
TABLE 2. (contd.)
Compound:
No. Substituents
794 9(11);19(=O,OH)
1204 19(=O,OMe);9~(H)
1259 19(=O,OH);7~(OH);9~(H)
12'
I ,
, I 17
1a'OH
2'
J'
17
"C02H8
~H
795 18 18
12
17
10
2 8'
, ,
3 5
8'
9
.
856
TABLE 2. (contd.)
Compound:
No. Substituents
67. Helifulvane
12
17
18 19
796 19(OH)
797 19(=0,OH)
798 19(=0,OH);11a(OH)
799 19(=0,OH);11a(OAc)
68. Tetrachyrane
¥o'7,.
12
11
-
2 \\ ,\' /
J 15
111
•
0
800 16(17)
847 16(17);15(=0)
805 7a(OH);16a(OH)
806 6a(OH);16a(OH)
TABLE 2. (contd.)
Compound:
No. Substituents
78. Villanovane
12 17
11
20
II
HI 19
875 13a(OH);17(OH);19(Oi-Val)
876 13a(OH);17(OAc);19(Oi-Val)
877 13a(OH);17(OH);19(OMeVal)
878 13a(OH);17(OAc);19(OMeVal)
879 13a(OH);17(OAc);3a(Oi-Val)
880 13a(OH);17(OAc);3a(OMeVal)
894 13a(OH);15a(OH)
69. Lycoctonine
\.
3
OH
TABLE 2. (contd.)
Compound:
No. Substituents
801
"" r::: OCHJ
' 'I
\\
\\\
OCHJ
OH
802 R=H
803 R=Anth
vrII. Undetermined Stereochemistry
79. Inulaefane
12 14
~ 1~
o
2
18
18
804 2(OHIll(OHI119(OHI
TABLE 2. (contd.)
Compound:
No. Substituents
15
~/'-- 0
14 \ I
.~16
~0
3
11
20 12
17
o
9
8
o
7
1B 19
940
999
TABLE 3. Diterpene compound numbers, the species from which these com-
pounds were reported and references (an asterisk indicates unpublished result)
Compound:
No. Species Reference
1. He1ichrysum mimetes 351
Mikania goyazensis 46
2. Pego1ettia senegalensis 104
3. Bejaranoa semistriata 44
Disynaphia halimifo1ia *
Kingianthus paradoxus 216
Stevia myriadenia 191
4. Bejaranoa semistriata 44
Trichogoniopsis morii 192
5. Mikania sessilifolia 48
6. Wyethia helenioides 202
7. Stylotrichium rotundifolium 148
8. Mikania officinalis 48
9. Lasiolaena morii 106
11. Grazielia intermedia 189

Lasiolaena morii
Lasiolaena santosii 99
12. Grazielia intermedia 189
13. Mikania goyazensis 46

14. Disynaphia halimifolia 67
16. Zexmenia gnaphaloides 125
19. Koanophyllon admantium 42
20. Koanophyllon cong1obatum 42
21. Lasiolaena santosii 99
22. Zinnia tenuiflora 215

Zinnia verticillata 215
23. Geigeria burkei 172

subsp. burkei var. burkei
Geigeria burkei 172
subsp. fruticulosa
Helichrysum mundii 171
Table 3. Diterpene Compound Numbers 151
TABLE 3. (contd.)
Compound:
Helichrysum nanum *
Helichrysum subfacultatum 171
Inula cuspidata 140
Mikania officinalis 48

Geigeria burkei 172
subsp. diffusa

subsp. burkei var. elata

Geigeria burkei 172
subsp. burkei var. intermedia

Geigeria burkei 172
Geigeria burkei 172
subsp. burkei var. zeyheri
Geigeria burkei 172
Geigeria burkei 172
32. Helichrysum Krebsianum 171
Helichrysum oreophilum 351
Helichrysum oxyphyllum 171
33. Geigeria burkei subsp. diffusa 172
34. Geigeria burkei subsp. diffusa 172

Geigeria burkei subsp. diffusa 172

subsp. fruticulosa
TABLE 3. (con/d.)
Compound:
38. Geigeria burkei subsp. burkei 172
var. zeyheri
39. Geigeria burkei subsp. burkei 172
var. burkei
Geigeria burkei subsp. burkei 172
var. zeyheri
40. Acanthospermurn australe 96
4l. Acanthospermurn australe 96
42. Melampodiurn longipilurn 434
44. Melampodiurn diffusurn 435
45. Melampodiurn diffusurn 435
48. Acanthospermurn australe 96
49. Ichthyothere ulei 107
5l. Ichthyothere ulei 107
55. Montanoa 1eucantha 382
subsp. arborescens
Montanoa leucantha 382
subsp. leucantha
Montanoa mollissima 382
Montanoa tomentosa 382
subsp. microcephala
subsp. tomentosa
subsp. xanthiifolia
56. Montanoa tomentosa 459
subsp. xanthiifolia
subsp. tomentosa
TABLE 3. (contd.)
Compound:
59. Baccharis trinervis 117
Centaurea cineraria *
Conyza canadensis *
Conyza ulmifolia *
Felicia erigeroides *
Heteromma simplicifolium *
Nidorella auriculata *
subsp. polycephala
Osteospermum barberia 151
Plagiocheilus prostratus 133
60. Centipeda orbicularis 128,133

Plagiocheilus prostratus 133
61. Conyza podocephala 154
62. Dimerostemma asperatum 214
Dimerostemma brasilianum 141
63. Dimerostemma asperatum 214
64. Dimerostemma brasilianum 141
65. Helichrysum calliconum 39
68. Achyroc1ine vargasiana *
Gnaphalium microcephalum *
Helichrysum Krebsianum *
Helichrysum odoratissimum 298
Helichrysum nudifo1ium 39
Senecio pseudoorientalis *
Senecio trichopterygius *
69. Helichrysum acutatum 40
70. Greenmaniella resinosa *
Helichrysum acutatum
Helichrysum Krebsianum 171
He1ichrysun odoratissimum *
73. Helichrysum subfalcatum 171
74. Liatris elegans 335
75. Liatris elegans 335
76. Hemizonia lutescens 93
Zexmenia gnaphaloides *
TABLE 3. (contd.)
Compound:
77. Acanthospermum hispidum 398
78. Brickellia eupatoriedes 59
79. Baccharis scoparia 57

Oxylobus arbutifolius 87
Oxylobus glanduliferus 6
80. Gymnosperma glutinosa 393
81. Oxylobus glanduliferus 6
82. Carterothamnus anomalochaeta 185
86. Madia sativa 100
87. Madia sativa 100
88. Hemizonia congesta 93

Hemizonia lutescens 93
89. Hemizonia congesta 93

Hemizonia lutescens 93
Madia sativa 100
95. Gutierrezia sphaerocephala 272

97. Brickellia diffusa 50

100. Pleurocoronis pluriseta 147
101. Brickellia argyrolepis 147

TABLE 3. (contd.)
Compound:
106. Brickellia coryrnbosa 158
Brickellia eupatoriedes 59
Brickellia squarrosa 158
107. Brickellia squarrosa 158
108. Brickellia coryrnbosa 158
Brickellia squarrosa 158
109. Brickellia squarrosa 158
1l0. Baccharis tucumanensis 477
111. Senecio erosus 209
112. Trichogoniopsis morii 192
113. Solidago sempervirens 430

114. Chrysothamnus nauseusus 70
118. Stevia jaliscensis 206
119. Brickellia vernicosa 29
Chrysothamnus nauseusus 70
Grindelia discoidea 471
121. Macowania glandulosa 163
Stevia salicifolia 170
122. Brickellia argyro1epis 147
124. Baccharis salicifolia 503
Bricke1lia veronicaefolia 222
125. Bricke1lia veronicaefolia 222
Brickellia paniculata 287
Brickellia sp. 59,286
128. Bricke11ia eupatoriedes 59
TABLE 3. (contd.)
Compound:
129. Bricke11ia veronicaefolia 158
Brickellia veronicaefo1ia 158
var. typica
Chrysothamnus nauseusus 70
130. Gutierrezia lucida 188
131. Gutierrezia 1ucida 188
132. Denekia capensis 180
Helichrysum confertum 180
Helichrysum sutherlandia 171
Palafoxia rosea 66
133. Palafoxia rosea 66

Palafoxia texana var. ambigua *
Palafoxia texan a var. ambigua *
Palafoxia texana var. ambigua *
136. Pa1afoxia rosea 66
137. Chromolaena collina 175
Fleischmannia deborabe11ae 68
138. Chromo1aena co11ina 175
139. Fleischmannia pycnocepha1oides 68
Geigeria burkei Harv. 172
Geigeria burkei Harv. 172
subsp. burkei var. zeyheri
Inula crithmoides
Koanophyl1on cong1obatum *
Podachaenium eminens 121
Si1phium connatum "
140. Hofmeisteria fasciculata 135
Stevia andina *
141. Nidore11a auriculata DC. 72
subsp. polycepha1a
Stevia andina "
142. Nidorel1a auricu1ata DC. 72
subsp. polycephala
Stevia andina *
143. Stevia monardaefo1ia 433
144. Koanophy11on conglobatum 135
145. Koanophyllon conglobatum 135
Stevia berlandiera 170
TABLE 3. (contd.)
Compound:
146. Koanophyllon conglobaturn 135
147. Koanophyllon cong1obaturn 135
149. Aristeguietia buddleaefolia 134
15I. Aristeguietia buddleaefolia 134
152. Bishovia boliviensis 186
153. Stevia monardaefolia 433
154. Stevia salicifolia 415
155. Smallanthus fruticosus 211
Helichrysurn coriaceurn *
Helichrysurn nudifoliurn var. *
nudifoliurn
Helichrysurn pinifoliurn 171
Helichrysurn vernurn 171
158. Solidago canadensis 16,17,73
Solidago gigantea
Solidago sempervirens 249
159. Gutierrezia dracunculoides 80

160. Gutierrezia mandonii 188
16I. Gutierrezia mandonii 188
162. Gutierrezia mandonii 188
164. Gutierrezia lucida 188
165. Chrysothamnus paniculatus 475
Grindelia boliviana 348
Grindelia camporurn 49,473,475
Grindelia chiloensis 294
Grindelia paludosa 49
Grindelia pulchella 294
Grindelia squarrosa 181
Grindelia stricta 49
Grindelia camporurn 473,475
Grindelia squarrosa 473,475
TABLE 3. (contd.)
Compound:
Heterotheca subaxillaris *
167. Chrysothamnus panicu1atus 475
Grindelia aphanactis 348
Grindelia acutifolia *
Grindelia camporum 49,473
Grindelia chi10ensis 294,348
Grindelia nauseosus 440
Grindelia perennis 348
Grindelia pu1chella 294
Grindelia robusta 440
Grindelia squarrosa 68,220,473
Haplopappus venetus 74
Heterotheca subaxillaris *253
Isocoma coronopifolia
Solidago petradoria *
168. Grindelia pu1chella 293
169. Grindelia stricta 49
170. Grindelia camporum 49
Grindelia humilis 441
172. Chrysothamnus panicu1atus 475
Grindelia humilis 441
173. Grindelia aphanactis 348

Grindelia squarrosa 220,473
Haplopappus tenuisecta 74
Heterotheca sUbaxillaris *253
Isocoma coronopifolia

Grindelia chi10ensis 294
Grindelia pu1chella 294
Solidago petradoria *
TABLE 3. (contd.)
Compound:
Grindelia camporum 475
178. Grindelia perennis 348
Isocoma coronopifolia 253
18l. Grindelia camporum 49

189. Chrysothamnus paniculatus 341,475
Grindelia acutifolia
Grindelia aphanactis *
Grindelia camporum 49,473,475
Grindelia pa1udosa 49
TABLE 3. (contd.)
Compound:
Grindelia stricta 49,475
Heterotheca subaxillaris *
191- Chrysothamnus panicu1atus 475
193. Solidago canadensis 17,73
194. Solidago canadensis 73
195. Eupatorium jhanii 289
Stevia rebaudiana 461
Eupatorium jhanii 289
200. Pa1afoxia rosea 66,250
201- Palafoxia rosea 250
202. Baccharis to1a 450
203. Lindheimera texana 337

Si1phium asteriscus 91
Silphium compositum *
Silphium integrifolium 91
Silphium perfoliatum 91
Silphium terebinthinaceum 91
204. Echinacea purpurea 88

Lindheimera connata
Lindheimera texana 337
Silphium asteriscus 91
Silphium compositum *
SIlphium connatum *
Si1phium integrifo1ium 91
Silphium perfoliatum 91
Si1phium terebinthinaceum 91
Trichogoniopsis morii
205. si1phium perfo1iatum 91

TABLE 3. (contd.)
Compound:
206. Silphiurn asteriscus 91
Silphiurn integrifoliurn 91
Silphiurn perfoliaturn 91
Silphiurn terebinthinaceurn 91
207. Silphiurn asteriscus 91

Silphiurn integrifoliurn 91
Silphiurn perfoliaturn 91
silphiurn terebinthinaceurn 91
208. Silphiurn perfoliaturn 91
210. Carterothamnus anoma1ochaeta 185
21l. Carterothamnus anomalochaeta 185
Silphiurn terebinthinaceurn 91

214. Nidorella hottentotica 155
220. Brickellia veronicaefolia 158
22l. Grindelia paludosa 49
Grindelia acutifolia
231- Relhania acerosa 90
TABLE 3. (contd.)
Compound:
236. Bedfordia salicinia 122
237. Bedfordia salicinia 122
238. Nidorella agria 72
239. Solidago gigantea var. serotina 15,401

Solidago serotina 14
240. solidago serotina 14
241. Solidago serotina 14
244. Solidago gigantea var. serotina 15,401
Solidago serotina 14
248. Centipeda orbicularis 128
249. Centipeda orbicularis 128
251. Nidorella resedifo1ia 72
255. Conyza stricta 376

Grangea maderaspatana
Koanophyllon admantium 42
256. Nidorella resedifolia 42
257. Macowania glandulosa 163
258. solidago altissima 143

Solidago virgaurea 291
TABLE 3. (contd.)
Compound:
259. Solidago altissima 143
Solidago rugosa 73
261- Solidago altissima 143
263. Solidago virgaurea 291
266. Solidago virga urea 291
271- Chrysothamnus panicu1atus 474
272. Othonna sedifolia *
Palafoxia rosea 66
Senecio variabilis *
273. Pa1afoxia rosea 66
Stevia salicifolia 170
274. Senecio subrubrif10rus 169

276. Chrysanthemoides monolifera 79
subsp. canescens
Garu1eum bipinnatum 156
Garu1eum pinnatifidum 156
Garuleum sonchifolium
Osteospermum auricula tum 151
Osteospermum barberiae 151
Osteospermum ciliatum 151
Osteospermum corymbosum 157
Osteospermum fruticosum 156
Osteospermum jucundum 151
Osteospermum junceum 156
Osteospermum muricatum 151
subsp. muricatum
Osteospermum rotundifolium 157
Senecio subrubriflorus 169
TABLE 3. (contd.)
Compound:
277. Garu1eum bipinnatum 156
Osteospermum auricu1atum 151
279. Chrysanthemoides mono1ifera 79
Chrysanthemoides mono1ifera 79
subsp. canescens
Senecio subrubrif10rus 79
285. Osteospermum fruticosum 156
286. Osteospermum barberiae 151
287. Osteospermum barberiae 151
subsp. canescens
Senecio subrubrif10rus 169
subsp. canescens
Osteospermum ci1iatum 151
Osteospermum incanum *
Osteospermum muricatum 151
subsp. muricatum
Osteospermum oppositifo1ium 156
Osteospermum po1yga1oides *
Osteospermum rotundifo1ium 157
Osteospermum scariosum 151
subsp. scariosum
Osteospermum thodei 151
291. Senecio subrubriflorus 169

TABLE 3. (contd.)
Compound:
292. Chrysanthemoides incana 79
Chrysanthemoides monolifera 79
Garuleum bipinnatum 156
Garuleum pinnatifidum 156
Garuleum sonchifolium
Osteospermum polygalioides 157
Osteospermum rotundifolium 157
Senecio sandersonii 173
Senecio subrubriflorus *
293. Garuleum bipinnatum 156
subsp. canescens
Helichrysum diosmifolium *
Osteospermum subulatum 157

subsp. canescens
Osteospermum auriculatum 151
Osteospermum ciliatum 151
Osteospermum thodei 151
Senecio sandersonii 173

297. Garuleum pinnatifidum 156

300. Achillea filipendulina 25
Dimorphotheca pluvialis 118
Mikania pyramidata 131
301. Dimorphotheca pluvialis 118

308. Croptilon divaricatum 252

309. Croptilon divaricatum 252
Pa1afoxia rosea 66
TABLE 3. (contd.)
Compound:
310. Osteospermum muricatum 151
subsp. muricatum

subsp. muricatum
subsp. muricatum
313. Palafoxia rosea 66,168
314. Palafoxia rosea 66,168,251
315. Pa1afoxia rosea 66,168
316. Solidago missouriensis 10
319. Inula roy Ie ana 34
320. Inula royleana 34
321. Inula royleana 34,254
322. Inu1a royleana 34,254
323. Inula royleana 34,254

324. Inu1a royleana 34
325. Dimorphotheca pluvialis ll8
326. Zexmenia gnaphaloides 125
327. Relhania acerosa 90
328. Austroeupatorium chaparense 146
329. Chrysothamnus viscidiflorus 370
330. Chrysothamnus viscidiflorus 370

Grindelia aegialitis 414
331. Baccharis sternbergiana 136
335. Morithamnus crassus 102

Relhania acerosa 90

TABLE 3. (contd.)
Compound:
337. Ayapana amygdalina 113
341 Ayapana amygdalina 113

347. Relhania acerosa 90
348. Acritopappus longifolius 85
353. Lasiolaena santosii 99
355. Ageratina dendroides 77
Pleurocoronis p1uriseta 62
356. Hartwrightia f10ridana 95
358. Eupatorium petio1are 223
360. Hap10pappus pectinatus 348
361. Pleurocoronis pluriseta 62
362. Achyrocline alata 43
363. Baccharis intermixta 178
364. Baccharis intermixta 178
Lasio1aena santosii 99
TABLE 3. (contd.)
Compound:
365. Acritopappus confertus 184
366. Acritopappus confertus 179,184
37l. Acritopappus confertus 184

38l. Acritopappus confertus 184
382. Acritopappus morii 179
385. Xanthocephalum linearifo1ium 110
388. Ageratum fastigiatum 53,126
389. Ageratum fastigiatum 53,126
390. Ageratum fastigiatum 126
39l. Ageratum fastigiatum 53

TABLE 3. (contd.)
Compound:
399. Acritopappus hagei 179

403. Xanthocepha1um 1inearifo1ium 110

404. Psiadia altissima 224
405. Conyza stricta 460
406. Austroeupatorium inulaefolium 177
407. Austroeupatorium inulaefo1ium 177


412. P1ana1toa lychnophoroides 203
413. P1ana1toa 1ychnophoroides 203
415. Desmanthodium fruticosum *
Stevia 1ucida Lag. var. Bipontini 448
416. Xanthocepha1um 1inearifo1ium 110
417. Austroeupatorium inu1aefo1ium 177
418. Austroeupatorium inu1aefolium 177
421. Stevia myriadenia 191
422. Ichthyothere connata 201

Viguiera bishopii 92
TABLE 3. (contd.)
Compound:
423. He1ianthus decapeta1us 98
424. He1ianthus angustifo1ius 98,409
He1ianthus decapeta1us 98
He1ianthus maximi1iani 280
He1ianthus occidenta1is
He1ianthus tuberosus 98
Ichthyothere connata 201
Ichthyothere 1atifo1ia 201
Ichthyothere termina1is 107
Mikania banisteriae 228
Viguiera steno1oba
425. He1ianthus angustifo1ius 98
He1ianthus maximi1iani *
He1ianthus occidenta1is
He1ianthus tuberosus 98
Mikania a1vimii 47
426. Ichthyothere termina1is 107
427. Ichthyothere termina1is 107
428. Austroeupatorium inu1aefo1ium 177

Stevia andina 350
Stevia aristata *
Stevia origanoides 221
429. Stevia berlandiera 170
Stevia sa1icifolia 221
430. Helichrysum confertum 180
Helichrysum suterlandii 171
431. Mikania a1vimii 47

435. Mikania pyramidata 131
436. Grazie1ia dimorpho1epsis 189

438. Mikania alvimii 47
TABLE 3. (contd.)
Compound:
441. Helichrysum sp. 171
442. Aspilia parvifolia 213
Baccharis oxydonta 116
Denekia capensis 180
443. Baccharis oxydonta 116
447. Helichrysum albirosu1atum 171
Helichrysum pinifolium 171
Helichrysum vernum 171
448. Helichrysum albirosulatum 171
449. Helichrysum albirosulatum 171
450. Gnaphalium gaudichaudianum
Gnaphalium undulatum 210
451. Coespeletia moritziana 145
Espeletia hartwegiana *
Espeletiopsis guacharaca 145
Olearia paniculata 426
Othonna sedifolia *
Solidago missouriensis 10,12
453. Solidago missouriensis 10,12
454. Printzia laxa 165
455. Baccharis tola 451
457. Schkuhria multiflora 101
458. Libanothamnus spectabilis 174

Libanothamnus wurdackii 174
459. Coespeletia lutescens 144

Coespeletia moritziana 145
Libanothamnus occultus 174
Libanothamnus spectabilis 174

461. Erigeron philadelphicus 487
TABLE 3. (contd.)
Compound:
462. Hartwrightia floridana 95
469. Mikania alvimii 47
473. Athrixia elata 150
475. Melampodium divaricatum 343
Solidago elongata 18
476. Symphyopappus reticulatus 190
477. Goyazianthus tetrastichus 60
479. Solidago elongata 18
484. Baccharis alaternoides 117

485. Symphyopappus compressus 190
487. Gochnatia paniculata 51

TABLE 3. (contd.)
Compound:
492. Syrnphyopappus reticulatus 190
493. Fleischmannia sinclairii 217

494. Stevia myriadenia 191
500. Solidago altissima 143,364,365,412
503. Fleischmannia sinclairii 217

Hartwrightia floridana 95
Neomiranda angularis *
504. Liatris scariosa 54
505. Haplopappus ciliatus 35,36
506. Hartwrightia floridana 95
507. Baccharis hutchisonii 57

Solidago arguta 7,386
508. Baccharis inc anum 284
Baccharis tricuneata var. lineata 200
509. Baccharis tricuneata (L. f.)Pers. 490
var. tricuneata
510. Baccharis articulata 283
Baccharis rhetinoides 503
511. Baccharis macraei

Brickellia annulosa 158
Grangea maderaspatana 423
Heteropappus altaicus 181
Koanophyllon adamanticum 42
Printzia laxa 165
Solidago juncea 318
512. Grangea maderaspatana 423
513. Conyza japonica 423
514. Hinterhubera imbricata 82

TABLE 3. (contd.)
Compound:
518. Baccharis ca1vescens 178

Baccharis chi1co 57
Baccharis crispa
Baccharis macraei
Baccharis sa1icifo1ia *
Baccharis sarothroides
Baccharis tricuneata var. 1ineata 200
Conyza ivaefolia 76
Conyza scabrida 83
Heteropappus althaicus 181
519. Olearia muelleri 352
520. Baccharis tricuneata var. lineata 200

Conyza ivaefolia 76
Conyza scabrida 83
Heteropappus altaicus 181
Printzia laxa 165
521. Baccharis conferta 295

523. Pulicaria gnaphaloides 443

Solidago juncea 318
Solidago rugosa 73

Baccharis gilliesii 503
Baccharis magellanica 503
Baccharis rhetinoides 503
Baccharis tricuneata 490
var. tricuneata
Liatris spicata
528. Baccharis tricuneata 283

var. tricuneata
529. Baccharis chilco 57

Baccharis gilliesii 503
Baccharis subdentata 116
Baccharis tricuneata 489,490
var. tricuneata
530. Baccharis tricuneata 489,490

var. tricuneata
531. Baccharis cassinaefo1ia 178

TABLE 3. (contd.)
Compound:
532. Baccharis cassinaefolia 178
533. Baccharis cassinaefolia 178
535. Symphyopappus reticu1atus 190
536. Symphyopappus reticu1atus 190
537. Synphyopappus reticu1atus 190
Acritopappus hagei 179
Morithamnus crassus 102
54l. Acritopappus hagei 179
542. Acritopappus teixeirae 179
Eupatorium turbinatum 350
Solidago a1tissima 143,4l3
544. Symphyopappus compressus 190
545. Solidago altissima 401,4l3
Solidago elongata 18,402
Solidago rugosa 73
546. Solidago elongata 18,402
55l. Symphyopappus compressus 190
Solidago rugosa 73
553. Solidago elongata 18,402
556. Solidago Shortii 8,11
557. Solidago Shortii 8,11
559. Baccharis trimera 334
560. Olearia heterocarpa 426
56l. Baccharis genistelloides 111
Baccharis microcephala 57
TABLE 3. (contd.)
Compound:
564. Bahianthus viscidus 84
565. Acritopappus teixeirae 179
Baccharis truncata 116
Bahianthus viscidus 84
566. Solidago rugosa 73
569. Baccharis a1aternoides 117
Baccharis polyphylla 117
570. Stevia polycephala 8
573. Conyza japonica 423

Conyza scabrida 83
Conyza stricta 470

576. Haplopappus angustifolius 339,462
Haplopappus foliosus 339,462
577. Haplopappus angustifolius 462
578. Solidago arguta 7,386
58l. Solidago arguta 7,386
583. Solidago arguta 7,263,386

Solidago itatiayensis 483
584. Solidago itatiayensis 483

585. Solidago itatiayensis 483
586. Gnaphalium undulatum 210
587. Garuleum sonchifolium 78
TABLE 3. (contd.)
Compound:
589. Sigesbeckia pubescens 397
590. Achillea filipendula 25
Aspilia ovalifolia *
Helianthus strumosus 327
Mikania alvimii 47
59l. Palafoxia arida 320
Sigesbeckia orientalis 28
592. Sigesbeckia orientalis 358
Sigesbeckia pubescens 358

595. Sigesbeckia puLescens 358
596. Liatris 1aevigata 325
597. Liatris laevigata 325
598. Liatris laevigata 325
599. Othonna f10ribunda 112
600. Othonna cylindrica 112
Othonna floribunda 112
60l. Brickellia eupatoriedes 59
61l. Solidago missouriensis 12

614. He1ichrysum chionosphaerum 45
TABLE 3. (con/d.)
Compound:
615. Solidago nemoralis 73
616. Mikania banisteriae 228
Solidago rugosa 73
618. Arctotis revoluta 119
Aspilia foliacea *
Athrixia pinifolia 164
Baccharis minutiflora 117
Balsamorhiza sagittata 130
Caramboa pithieri *
Coespeletia marc ana 145
Espeletia garciae
Espeletia uribei 144
Espeletiopsis purpurascens 145
Espeletiopsis tachirensis 145
Helichrysum davyi *
Libanothamnus granatesianus 174
Libanothamnus tamanus 174
Lychnophora sellowii 204
Montanoa pteropoda 123
Montanoa tomentosa *
Ruilopezia jahnii 144
Ruilopezia lindenii 144
Ruilopezia marcescens *
Ruilopezia palanoides *
Ruilopezia rU1Z11 *
Tamania chardonii *
619. Abrotanella nivigena 13
Arctotis revoluta 119
Aspilia foliacea *
Aspilia jolyana *
Aspilia parvifolia 213
Austroeupatorium inulaefolium 177
Baccharis quitensis *
Cacalia bulbifera 257,373
Campovassouria bupleurifolia *
Coespeletia lutescens 144
Coespeletia marcana 145
Critonia daleoides 217
Disynaphia multicrenulata *
Espeletia garciae
Espeletia grandiflora *
Espeletia schultzii 132
Espeletia wedellii 144
Espeletiopsis garciae 145
Espeletiopsis glandulosa 145
Goyazianthus tetrastichus 60
TABLE 3. (contd.)
Compound:
Helianthus giganteus 98
Helichrysurn davyi *
Helichrysurn dendroideurn 373
Helichrysurn heterolasiurn 39
Helichrysurn miconiifoliurn 171
Helichrysurn pilosellurn 351
Helichrysurn vernurn *
Ichthyothere rufa 201
Ichthyothere terminalis 201
Libanothamnus granatesianus l74
Libanothamnus neriifo1ia 144
Mikania arrojadoi 142
Mikania belemii 48
Mikania luetzelburgii 48
Mikania sessilifolia 48
Oyedaea lanceo1ata 166
Oyedaea rusbyi *
Oyedaea verbesinoides *
Perymeniurn ecuadoricurn 162
Perymeniurn featherstoni *
Perymeniurn serraturn *
Polymnia fruticosurn 161
Polymnia pyramidalis 161
Ruilopezia bromeloides *
Ruilopezia figerasii *
Ruilopezia paltonioides *
Smallanthus fruticosus 211
Smallanthus uveda1ia 211
Steiractinia mollis 115
Steiractinia sodiroi 124
Tamania chardonii *
Viguiera grammatoglossa *
Wedelia grandiflora 120
Wedelia hookeriana 193
620. Campovassouria bupleurifo1ia 146
Espe1etiopsis guacharaca 145
Helichrysurn miconiifoliurn 171
621- Baccharis minutiflora 117
622. Baccharis quitensis 117
Polymnia fruticosa 116
623. Helichrysurn dendroideurn 374
Aspilia jolyana *
Aspilia pluriseta subsp. pluriseta *
Aster baker anus 478
Austroeupatoriurn inulaefoliurn 139
Baccharis ramosissima 116
TABLE 3. (contd.)
Compound:
Cacalia bulbifera 257
Campovassouria bupleurifolia 146
Disynaphia mu1ticrenu1ata *
Espe1etia garciae
Espeletia grandiflora
Espeletia neriifolia
Gnaphalium undu1atum 219
Grazielia intermedia *
Helianthus annuus 446
Helichrysum davyi *
Helichrysum heterolasium 39
Helichrysum miconiifo1ium 171
Helichrysum pallidum 171
Helichrysum pilosellum 351
Ichthyothere ulei 201
Libanothamnus neriifolia 144
Mikania belemii 48
Mikania micrantha *
Mikania sessi1ifolia 48
subsp. tomentosa
Oyedaea buphthalmoides
Oyedaea lanceo1ata 166
Oyedaea rusbyi *
Perymenium ecuadoricum 162
Perymenium klattianum *
Ruilopezia figueirasii *
Smallanthus glabratus 108
Smallanthus uvedalia 211
Solidago multiradiata var. *
multiradiata
Solidago rugosa 73
Viguiera grammatoglossa *
Zaluzania angusta *
Zaluzania subcordata *
625. Abrotanel1a nivigena 13

Arctotheca prostata *
Arctotis revoluta 119
TABLE 3. (contd.)
Compound:
Aspilia floribunda
Aspilia foliacea *
Aspilia jo1yana *
Aspilia mossambicensis *
Aspilia p1uriseta *
Aspi1ia p1uriseta 94
subsp. p1uriseta
Aspi1ia ridde11ii *
Aster baker anus 478
Aster p1eiocepha1us *
Athrixia e1ata 150
Austroeupatorium inu1aefo1ium 177
Baccharis concinnia 116
Baccharis elliptica *
Baccharis intermixta 178
Baccharis po1yphylla 178
Baccharis pylicoides 57
Baccharis quintensis 116
Baccharis ramosissima 116
Baccharis sa1zmannii 178
Caca1ia bu1bifera 257
Campovassouria bup1eurifo1ia 146
Caramboa pithieri *
Caramboa trugi11ensis *
Chroma1aena cryptantha *
Coespe1etia 1utescens 144
Coespe1etia marcana 145
Coespe1etia moritziana 145
Critonia da1eoides 217
Critonia hebebotrya *
Disynaphia mu1ticrenu1ata 137
Enhydra f1uctuans 422
Espe1etia figueirasii 480
Espe1etia f1occosa 480
Espe1etia garciae
Espe1etia grandif10ra 428
Espe1etia moritziana 480
Espe1etia schultzii 132
Espe1etia uribei 144
Espe1etiopsis garciae 145
Espe1etiopsis glandu10sa 145
Espe1etiopsis purpurascens 145
Espe1etiopsis tachirensis 145
Eupatorium petio1are 223
Gnapha1ium oligandrum 210
Gnapha1ium undu1atum 210
Grazie1ia dimorpho1epsis 189
Grazielia intermedia *
Grazielia serrata 189
He1ianthopsis bishopii 198
He1ianthopsis microphy11a 198
He1ianthopsis utcubambensis 198
TABLE 3. (contd.)
Compound:
Helianthus angustifolius 98
Helianthus annuus 264,358,491
Helianthus debilis 332
subsp. cucumerifolius
Helianthus debilis subsp. debilis 411
Helianthus decapetalus 31,98
Helianthus occidentalis 105
var. dowellianus
Helianthus giganteus 31,98
Helianthus heterophyllus 321
Helianthus hirsutus 31
Helianthus niveus subsp. 410
canescens
Helianthus nuttallii 31
Helianthus petiolaris 327
Helianthus radula 326
Helianthus rigidus
Helianthus simulans 332
Helianthus tuberosus 98
Helichrysum argentissimum 171
Helichrysum argyrolepis *
Helichrysum aureum var. monocepha1um
Helichrysum bellum 167
Helichrysum chionosphaerum 45
Helichrysum confertum
Helichrysum cooperi
Helichrysum davyi *
Helichrysum fulvum 208
Helichrysum miconiifolium 171
Helichrysum platypterum 167
Helichrysum refluxum 86
Helichrysum subulifolium 351
Helichrysum vernum 171
Heterocondylus grandis *
Ichthyothere cunabi
Ichthyothere latifolia 201
Iostephane heterophylla *
Lagascea rigida 89
Lasianthaea podocephala 124
Libanothamnus spectabi1is 174
Loxothysanus sinuatus 129
Melampodium paniculatum *
Melampodium perfoliatum *
Mikania belemii 48
TABLE 3. (contd.)
Compound:
Mikania cordata 131
Mikania hirsutissima 396
var. hirsutissima
Mikania micrantha *
Mikania monagasensis 383,384
Mikania schenkii *
Montanoa atriplicifolia 64
Montanoa frutescens *
Montanoa tomentosa subsp. 227
xanthiifolia
Othonna cylindrica 112
Othonna floribunda 112
Othonna sedifolia *
Oyedaea boliviana 166
Oyedaea buphthalmoides *
Oyedaea lanceolata 166
Oyedaea rusbyi *
Perymeniopsis ovalifolia 103
Perymenium discolor
Perymenium feathers toni *
Perymenium klattianum 103
Perymenium serratum *
Polymnia fruticosum 161
Polymnia maculata var. maculata 371
Robinsonia thurifera 339
Ruilopezia rUlZll *
Simsia dombeyana *
Simsia holwayi *
Smallanthus reparius 109
Smallanthus siegesbeckia *
Smallanthus uvedalia 114,211
Solidago juncea
Solidago missouriensis 369
Solidago multiradiata *
Solidago r igida 11,369
Solidago rugosa 73
Stevia andina *
Stevia monardaefolia 433
Stevia setifera 69
Tetrachyron manicata *
Tetrachyron orizabaensis 411
var. websteri
Tithonia longiradiata *
Verbesina angustifolia 160
TABLE 3. (contd.)
Compound:
Verbesina oncophora 160
Vernonia divaricata *
Vernonia venosissima *
Viguiera cordata *
Viguiera cordifolia 199
Viguiera dentata 275
Viguiera exce1sa 242
Viguiera grammatog1ossa 199
Viguiera hypargyrea 5
Viguiera inc ana *
Viguiera insignis 245
Viguiera linearifolia *
Viguiera linear is 454
Viguiera macu1ata 241
Viguiera oaxacana 242
Viguiera pazensis *
Viguiera porteri 331
Viguiera potosina 276
Viguiera procumbens *
Viguiera trichophy11a *
Wede1ia buphtha1mif1ora 455
Wede1ia ca1ycina 328
Wedelia glauca 405
Wede1ia grandif10ra 120
Wede1ia he1ianthoides 120
Wedelia hispida 328
Wede1ia hookeriana 193
Wede1ia scaberrima 476
Wedelia speciosa 182
Wedelia tri10bata 120,213
Wedelia vi110sa *
Za1uzania angusta *
Za1uzania cinarescens *
Za1uzania discoidea *
Za1uzania subcordata *
Za1uzania tri10ba *
Zexmenia hispida 124

627. Mikania sessi1ifo1ia 48
Rui10pezia jahnii 144
628. Bedfordia sa1icinia 122
He1ichrysum dendroideum 374
629. He1ichrysum aureum var. 180

monocepha1um
He1ichrysum cooperi 180
He1ichrysum hetero1asium 39
630. Sma11anthus uveda1ia 114
Wede1ia tri10bata 120,213
631. Wedelia tri10bata 114,120
Wu1ffia macu1ata *
TABLE 3. (contd.)
Compound:
632. Wedelia trilobata 114,120
Wulffia maculata *
633. Smallanthus uvedalia 114
Wedelia trilobata 120
636. Aspilia p1uriseta subsp. p1uriseta 94
637. Sciadocepha1a schultze-rhonhofiae 217
639. Viguiera stenoloba 237,243
640. Helichrysum aureum var. 180
monocephalum
Helichrysum cooperi 180
Helichrysum davyi *
Helichrysum ruderale 171
641. Aster tanacetifo1ius *
Smal1anthus uvedalia 114
Stevia eupatoria 416
642. Helianthus decapetalus 98
643. Smallanthus fruticosus 211
Smallanthus uveda1ia 114
644. Smal1anthus fruticosus 211
Smal1anthus glabratus 108
Smal1anthus uveda1ia 114
645. Sma11anthus uvedalia 114
Baccharis concinna 116
Baccharis intermixta 178
Disynaphia multicrenulata 137
Enhydra fluctuans 421
Espeletia grandiflora *
TABLE 3. (contd.)
Compound:
Espeletia humbertii 479
Espeletia littlei 479
Espeletia tenor 394
Espeletia weddellii 394
Helianthus debilis subsp. 332
cucumerifolius
Helianthus grosseserratus 332
Helianthus niveus subsp. canescens 410
Helianthus nuttallii subsp. 367
nuttallii
Ichthyothere terminalis *
Ruilopezia ruizii *
Viguiera maculata 241
Viguiera potosina 276
Wedelia calycina 328
Wedelia scaberrima 476
647. Mikania arrojadoi 142

Espeletia curialensis *
Helichrysum aureum var. 180
monocephalum
Helichrysum miconiifo1ium 171
He1ichrysum pa11idum 171
TABLE 3. (contd.)
Compound:

Ruilopezia figuerasii *
Tamania chardonii *
649. Aster tanacetifolius *
Baccharis concinna 116
Caramboa pithieri *
Disynaphia multicrenulata *
Helianthus angustifolius 98
cucumerifolius
Helianthus debilis subsp. debilis 411
xanthiifolia
Oyedaea rusbyi *
Perymenium feathers toni *
Perymenium ovalifolia *
Polymnia fruticosum 161
Smallanthus uvedalia 211
Stevia monardaefolia 433
Tamania chardonii *
Tetrachyron orizabaensis 411
var. websteri
Viguiera pazensis 205
Viguiera quinqueradiata 240
Wedelia buphthalmiflora 455
TABLE 3. (contd.)
Compound:
Wedelia helianthoides 120
Wedelia pinetorum
Zexmenia pinetorum
650. Aspilia jolyana
Aspilia ovalifolia
*
Aspilia parvifolia
*
213
Aspilia pluriseta subsp. 94
pluriseta
Aster pleiocephalus *
Baccharis salzmannii 178
Grazielia dimorpholepsis 189
Grazielia intermedia 189
Helianthus occidentalis subsp. 105
dowellianus
Ichthyothere terminalis 107,201
Lagascea rigida 89
Stevia bupthalmiflora
Viguiera guingueradiata 240
Wedelia scaberrima 476
Wedelia villosa *
651. Aspilia jolyana *
Baccharis elliptica *
Caramboa pithieri *
Ichthyothere terminalis 107,201
Ruilopezia ru~z~~ *
Stevia bupthalmiflora
Tamania chardonii *
Wedelia helianthoides *
TABLE 3. (con/d.)
Compound:
Wede1ia hookeriana 193
652. Aspi1ia p1uriseta subsp. 94
p1uriseta
Austroeupatorium inu1aefo1ium 139
Campovassouria bup1eurifo1ia 146
Disynaphia mu1ticrenu1ata *
Enhydra f1uctuans 421
Espe1etiopsis garciae 145
Espe1etiopsis g1andu1osa 145
Grazie1ia intermedia *
He1ianthus annuus 264
Mikania sessi1ifo1ia 48
Montanoa frutescens
Stevia buptha1mif1ora
Tamania chardonii *
653. Ichthyothere connata 201

Ichthyothere 1atifo1ia 201
Mikania 1uetze1burgii 48
654. Aspi1ia p1uriseta subsp. 94
p1uriseta
Loxothysanus sinuatus 129
Mikania cordata 131
655. He1ianthus debi1is subsp.

curcumerifo1ius
Mikania be1emii 48
Mikania 1uetze1burgii 48
Mikania ob1ongifo1ia 482
Mikania sessi1ifo1ia 48
xanthiifolia
Perymeniopsis ova1ifo1ia 103
Wedelia g1auca 405
Wede1ia tri10bata 120
656. Viguiera porteri 331

Wede1ia ca1ycina 328
Wede1ia grandif10ra 120
657. Mikania cordata 131

TABLE 3. (contd.)
Compound:
658. Aspilia foliacea *
Solidago rugosa 73
Aspilia pluriseta subsp. *
pluriseta
Baccharis ramoisissima *
Solidago rugosa 73
660. Aspilia parvifolia *
Baccharis ramoisissima *
Solidago rugosa 73
661. Baccharis concinna 117
662. Wedelia trilobata 213
663. Wedelia tri10bata 213
664. Grazielia intermedia *
665. Aspilia floribunda

Aspilia foliacea *
Campovassouria bupleurifolia 146
Oyedaea rusbyi *
Viguiera trichophylla *
Wedelia grandiflora *
Wedelia pinetorum *
666. Ichthyothere terminalis *

667. Wedelia hookeriana 193
668. Espeletiopsis tachirensis 145

Ruilopezia ruizii *
Wedelia helianthoides
TABLE 3. (contd.)
Compound:
669. Campovassouria bupleurifolia 146
Oyedaea rusbyii *
67l. Adenostemma caffrum 127

Adenostemma lavenia 230
Amphiachyris dracunculoides *
Eupatorium album 127
Grazie1ia serrata 189
672. Adenostemma 1avenia 230
673. Adenostemma caffrum 127
Eupatorium album 127
Adenostemma lavenia 230
675. Ichthyothere terminalis 107
678. Atractylis gummifera 239
Xanthium strumarium 232
Xanthium strumarium var. 238
strumarium
679. Wedelia asperrima 408
680. Wedelia asperrima 408
68l. Atractylis gummifera 239
Wedelia glauca 456
682. Stevia rebaudiana 362
683. Stevia rebaudiana 361,362
685. Stevia rebaudiana 361,362
690. Athrixia elata 150
TABLE 3. (contd.)
Compound:
Doronicum hungaricum *
Espeletia littlei
Espeletia neriifolia
Espeletia timotensis
Espeletia schultzii 132,218
Eupatorium deltoideum
Gnaphalium oligandrum 210
Helianthus maximiliani
Helichrysum aureum var.
monocephalum
Helichrysum platypterum 171
Helichrysum refluxum *
Helichrysum ruder ale 171
Lagascea rigida 89
Lasianthaea podocephala 124
xanthiifolia
Othonna cylindrica *
Oyedaea rusbyi *
Polymnia maculata var. maculata 371
Riencourtia oblongifolia *
Ruilopezia jahnii *
Ruilopezia lindenii *
Ruilopezia margarita 481
Ruilopezia ru~z~~ *
TABLE 3. (contd.)
Compound:
Tithonia longiradiata *
Verbesina angustifolia 160
Viguiera dentata 92
Viguiera excelsa 242
Viguiera grammatoglossa
Viguiera linearis 454
Viguiera ins ignis 245
Viguiera oaxacana 242
Viguiera procumbens 92
Viguiera stenoloba var.
chihuahuensis
Wede1ia grandiflora 120
Wedelia hispida 328
Zaluzania disco idea *
Zaluzania subcordata *
Zaluzania triloba *
Zexmenia hispida 124
69l. Helianthus maximiliani
Ruilopezia ruizii *
Viguiera excelsea 242
Viguiera latibracteata
Viguiera linearis 454
695. Ambrosia hispida 322
TABLE 3. (contd.)
Compound:
Ruilopezia jahnii *
Ruilopezia ruizii *

Mikania arrojadoi *
697. Baccharis minutiflora 117
Helichrysum dendroideum 374
700. Espeletia figueirasii 480
Espeletia floccosa 480
Espeletia moritziana 480
Helianthus occidentalis var. 105
dowellianus
Helianthus debilis Nutt. 332
subsp. cucumerifolius
nuttallii
Othonna sedifolia *
Ruilopezia rU1Zll *
TABLE 3. (contd.)
Compound:
cucumerifolius
Ruilopezia ruizii *
703. Helianthus debilis subsp. 332
cucumerifolius
dowellianus
704. Polymnia canadensis 187
71l. Smallanthus uvedalia 117
713. Baccharis elliptica *
Disynaphia multicrenulata 137
Othonna sedifolia *
714. Baccharis elliptica *
dowellianus
715. Perymenium ecuadoricum 163
716. Espeletia uribei 144
Aspilia pluriseta
TABLE 3. (contd.)
Compound:
Cacalia bulbifera 257
Espeletia littlei
Espeletia schultzii 132,219
Helianthus argophyllus 493
Helianthus salicifolius 324
Helichrysum refluxum *
Perymenium serratum *
Robinsonia gayana *
Zaluzania cinarescens *
722. Helichrysum davyi *
Ichthyothere terminal is 107
723. Coespeletia marc ana 145
cucumerifolius
Perymenium discolor
Steiractinia mollis *
Viguiera linearis
Viguiera stenoloba
Zaluzania angustifolia
724. Helianthus angustifolius 409
Helianthus rigidus 324

TABLE 3. (contd.)
Compound:
Peteravenia mal vaefolia *
726. Trichogoniopsis morii 192
727. Hymenopappus newberryi 207
728. Helianthus occidentalis 332
Helichrysum diosmifolium 366
Sigesbeckia pubescens 285
Steiractinia mollis *
73l. Baccharis minutiflora 117
738. Baccharis minutif10ra 117

74l. Sigesbeckia pubescens 397
746. Helianthus debilis subsp. 332
cucumerifolius
TABLE 3. (contd.)
Compound:
748. Adenostemma 1avenia 230,336
749. He1ianthus radu1a 326
750. Coespe1etia marcana 145
Espe1etia hartwegiana *
Rui10pezia figueirasii *
Rui10pezia marcescens *
Rui10pezia pa1tonioides *
Rui10pezia ruizii *
Tamania chardonii *
Rui10pezia 1indenii 144
Espe1etia hartwegiana *
Rui10pezia figueirasii *
Rui10pezia marcescens *
Rui10pezia ruizii *
Tamania chardonii *
753. Coespe1etia 1utescens 144
Coespe1etia marcana 145
Rui10pezia 1indenii 144
Tamania chardonii *
754. Athrixia phy1icoides 164
755. Athrixia arachnoidea 150

Athrixia e1ata 164
Athrixia phy1icoides 164
756. Athrixia phy1icoides 164
TABLE 3. (contd.)
Compound:
757. Athrixia phylicoides 164
758. Atractylis gummifera 239

763. Gnaphalium undulatum 213

764. Helichrysum dendroideum 373

Dimorphotheca pseudoaurantiaca 199
Nidorella anomala 153
Viguiera grammatoglossa 199
Viguiera pazensis *

768. Viguiera insignis 245
769. Nidorella anomala 153

773. Montanoa tomentosa subsp. 351

xanthiifolia
Viguiera grammatoglossa 199,425
774. Dimorphotheca aurantiaca 199

Helianthopsis bishopii 198
Helianthopsis microphylla 198
Helianthopsis utcubambensis 198
xanthiifolia
TABLE 3. (contd.)
Compound:
Senecio asperulus *
Stevia aristata *
Viguiera cordifolia 199
Viguiera grammatoglossa 199
Viguiera pazensis *
Peteravenia malvaefolia *
Peteravenia schultzii *
777. Viguiera bishopii 92

783. Helichrysum chionosphaerum 45
784. Helianthus occidental is 331

Helianthus decapetalus 31,98
787. Helianthus dec ape talus 98
788. Helianthus dec ape talus 98

791. Helianthopsis bishopii 198

Helianthopsis microphylla 198
Helianthopsis utcubambensis 198
Helianthus annuus 31,392,491
cucumerifolius
dowellianus
TABLE 3. (contd.)
Compound:
Helianthus tomentosus 31
Viguiera lanceolata 92
Viguiera paz ens is 92
Viguiera procumbens 92
Viguiera trichopylla *
792. Helianthus annuus 387
Helianthus californicus 282
Helianthus ciliaris 37
Helianthus niveus subsp. canescens 410
nuttallii
793. Helianthus radula 326
794. Viguiera bishopii 92

Viguiera trichophylla *
795. Helianthus radula 326
796 Helichrysum chionosphaerum 45

Mikania arrojadoi *
797. Helichrysum chionosphaerum 45
798. Helichrysum fulvum 208
799. Helichrysum fulvum 208

800. Helianthus debilis subsp. debilis 411
Montanoa tomentosa subsp.
xanthiifolia
Tetrachyron orizabaensis var. 411
websteri

804. Eupatorium inulaefolium 23
805. Eupatorium album 323

806. Eupatorium album 323
TABLE 3. (contd.)
Compound:
807. Piqueria trinervia 354
808. Stevia origanoides 221
809. Stevia andina *
812. Eupatorium petaloideum 336
818. Wedelia calycina 328

819. Wedelia calycina 328
820. Helianthus strumosus 327
Mikania triangularis 360
821. Helianthus strumosus 327
822. He1ianthus petio1aris 327
823. Helianthus hirsutus 327
824. Helianthus hirsutus 327
828. Austroeupatorium inu1aefolium 406
830. Critonia daleoides 217

Critonia hebebotrya *
Gutierrezia sarothrae 197
831. Gutierrezia sarothrae 197

TABLE 3. (contd.)
Compound:
842. Gutierrezia grandis 271
Gutierrezia sarothrae 197
846. Baccharis inc anum
Baccharis kingii 196
Conyza scabrida 83
847. Viguiera maculata 241
848. Ophryosporus chilca 152
849. Ophryosporus chilca 152
851. He1ianthus annuus 446

857. F1eischmannia viscidipes 81
858. Fleischmannia viscidipes 81
Oxylobus canescens *
TABLE 3. (contd.)
Compound:
866. Wedelia regis 75
869. Aspilia floribunda 75
870. Aristeguieta pseudoarborea 194
871. Aristeguietia pseudoarborea 194
875. Villanova titicaensis 195
876. Villanova ti ticaensis 195
88l. Trichogonia sa1vaiaefolia 183
Trichogonia villosa 183
882. Trichogonia salvaiaefolia 183
883. Trichogonia villosa 183
887. Trichogonia salviaefolia 11

TABLE 3. (contd.)
Compound:
89l. Trichogonia villosa 183
892. Aspilia mossambicensis *

893. Viguiera pazensis 205
894. Viguiera pazensis 205
895. Stevia ovata 355,464

Stevia paniculata 501
896. Stevia ovata 355




900. Conyza scabrida 83
90l. Conyza scabrida 83

Conyza scabrida 83
91l. Conyza scabrida 83
TABLE 3. (contd.)
Compound:

Pulicaria angustifolia 463
926. Lasianthaea podocephala 124

Melampodium perfoliatum 159
Mikania banisteriae 228
927. Zexmenia phyllocephala 124

928. Zexmenia phyllocepha1a 124
929. Zexmenia phyllocepha1a 124
930. Zexmenia phy11ocepha1a 124
932. Zexmenia phy11ocepha1a 124
938. Eupatorium villosum 379
939. Melampodium divaricatum *

Melampodium paludosum *
Melampodium perfoliatum 159

xanthiifolia
TABLE 3. (contd.)
Compound:
xanthiifolia
945. Dornoicum macrophyllum 3
Doronicum microphyllum 285
946. Espeletia wedellii 394
948. Balsamorhiza sagittata 130
949. Balsamorhiza sagittata 130

950. Heteropappus altaicus 181
95l. Heteropappus altaicus 181
955. Grindelia squarrosa 473
956. Grindelia squarrosa 473

957. Helianthopsis bishopii 198
958. Macowania glandulosa *
Oxylobus arbutifolius 87
959. Oxylobus adscendens 87
96l. Solidago altissima 143
962. Baccharis tucumanensis 442
963. Baccharis grandicapitulata 57
965. Baccharis eggersii 57
966. Baccharis eggersii 57
967. Baccharis hutchisonii 57
968. Baccharis nitida 57
TABLE 3. (con/d.)
Compound:
971. Aster alpinus 97
972. Aster alpinus 97
973. Tridax peruviensis 97
974. Gutierrezia gil1iesii 348
Gutierrezia grandis 271
Gutierrezia sobrigii 347
975. Gutierrezia grandis 271

976. Helichrysum refluxum 86
977. Rudbeckia fulgida var. fu1gida 329
978. Sma11anthus glabratus 108
979. Smallanthus glabratus 108

984. Ageratina tristis 58
985. Pulicaria angustifolia 463
989. Viguiera potosina 276
990. Viguiera potosina 276
Eupatorium maretiana 2
992. Bricke11ia vernicosa 2

997. Disynaphia multicrenulata 137
TABLE 3. (contd.)
Compound:
998. Stevia eupatoria 416
999. Hebec1inium macrophyllum 77

1002. Mikania congesta 330
1006. Melampodium leucanthum 436
1007. Viguiera stenoloba 243
1008. Eupatorium inulaefolium 23
1012. Piptothrix jaliscensis 269
1013 . Piptothrix j aliscensis 269
1014. Piptothrix sinaloae 269
1015. Austrobrickellia patens 349
1020. Stevia lemmonia 170
1021. Stevia berlandiera 170
1022. Stevia ber1andiera 170
1023. Stevia and ina *
107· . Stevia salicifolia 170
TABLE 3. (contd.)
Compound:
1027. Chromolaena laevigata 390

Baccharis sarothroides 22
Baccharis vaccinoides 22
1034. Baccharis sarothroides 22
1035. Grindelia boliviana 348
1037. Gutierrezia gilliesii 348

Gutierrezia solbrigii 347

Gutierrezia solbrigii 347

1040. Gutierrezia spathulata 348
1045. Haplopappus glutinosus 348
1046. Haplopappus pectinatus 348
1050. Hap10pappus pectinatus 348

1054. Solidago petradoria 348
TABLE 3. (con/d.)
Compound:
1055. Hap10pappus paucidentatus 348
1056. Haplopappus paucidentatus 348
1057. Hap10pappus paucidentatus 348
1062. Solidago gigantea var. serotina 317

1069. Liatris spicata 29
1071. Solidago juncea 318
1077 . Solidago gigantea var. serotina 385
1083. Gutierrezia texana 274
TABLE 3. (contd.)
Compound:
1086. Gutierrezia texan a 274


1096 . Montanoa tomentosa 432

tomentosa

tomentosa
tomentosa
He1ichrysum confertum 180
1103. He1ichrysum confertum 180

1104. He1ichrysum confertum 180
1105. He1ichrysum albirosulatum 180
1106. He1ichrysum albirosu1atum 180
1107. He1ichrysum albirosulatum 180

He1ianthus decapetalus var. 31
multif10rus
1109. Cronquistianthus bishopii 61
TABLE 3. (contd.)
Compound:
1110. Cronquistianthus bishopii 61
1111. Solidago drummondii 65
1112. Mikania perip1ocifolia 296
1113. Mikania perip1ocifolia 296
1114. Mikania periplocifolia 296
1115. Mikania periplocifolia 296
1116. Bejaranoa balansae 453

1117. Bejaranoa balansae 453
1118. Chiliotrichium rosarinifolium 346

1120. Aspi1ia parvifolia 182
1121. Vernonia glabra var. glabra 55
1122. Heterochrysum oreophilum 351
1123. Heterochrysum oreophilum 351
1124. Acanthospermum australe 138
1125. Solidago flexicaulis 65

Solidago racemosa 65
Solidago drummondii 65
1129 Solidago drummondii 65

1130. Gutierrezia solbrigii 347
1133. Nordophyllum lanatum 346
1134. Nordophyllum lanatum 346

TABLE 3. (contd.)
Compound:
1138. Helichrysum nudifolium var. 351
nudifolium
1139. Oxylobus glanduliferus 6
1140. Grindelia discoidea 472
1143. Eupatorium salvia 339

1144. Eupatorium salvia 339
1146. Chrysothamnus nauseosus 471
Grindelia discoidea 471
1147. Helichrysum confertum 180

1151. Helichrysum nudifolium var. 351
nudifolium
1152. He1ichrysum nudifolium var. 351
nudifolium
1153. Isocoma coronopifolia 253
1154. Isocoma coronopifo1ia 253


1161. Palafoxia texana 290
1162. Palafoxia texana 290
1163. Eupatorium turbinatum 350
1164. Grindelia aegialitis 414
1165. Baccharis pingraea 503
TABLE 3. (contd.)
Compound:
Baccharis salicifolia 503
1l66. Baccharis pingraea 503
1l70. Baccharis salicifolia 503
1l7l. Baccharis pingraea 503

1l72. Baccharis salicifolia 503
1l73. Baccharis trinervis 27

1l74. Gutierrezia solbrigii 347
1l75. Haplopappus pectinatus 348
1177 . Haplopappus pectinatus 348
1l80. Acritopappus morii 179

1l85. Mikania alvimii 47
1l86. Palafoxia rosea 26
TABLE 3. (contd.)
Compound:
1194.. Gutierrezia spathulata 348

1203. Baccharis pingraea 503

1204. Helichrysum argolepis *

1209. Baccharis polifera 503
1210. Baccharis polifera 503
1211. Eupatorium turbinatum 350
1212. Chiliotrichium rosmarinifolium 346

Nardophyllum lana tum 346
1217. Nardophyllum lanatum 346

1222. Baccharis incarum 449
1223. Pulicaria salviifolia 403

TABLE 3. (contd.)
Compound:
1229. Baccharis rhomboidalis 452
1231. Baccharis rhetinodes 503
1234. Pulicaria sa1viifolia 404
1235. Pulicaria sal viifolia 404
1239. Baccharis grandicapitulata 57

1244. Baccharis mage11anica 503
1245. Baccharis magellanica 503
1247. Gochnatia glutinosa 278
1248. Gochnatia glutinosa 278

1249. Senecio hypochoerideus 71
1250. Mikania triangularis 360

1251. Helichrysum setosum 351
TABLE 3. (contd.)
Compound:
1255. Ruilopezia margarita 481
[=Espe1etia margarita)
1256. Rui10pezia margarita 481
1259. Helianthus grosseserratus *
Helianthus 1aciniatus *
Helianthus rigidus *
Figure 1. Structures of Diterpenes 219
1. Geranylnerol
OH
C R
4
1 Rl = R2 R3 = R4 = H
2 Rl = R3 R4 H, R2 = OH
3 Rl = R2 R3 H, R4 = OH
4 Rl = R4 OH, R2 = R3 = H
984 Rl R2 H, R3 = OAe, R4 OH
1109 Rl R2 OH, R3 R4 = H
1110 Rl R2 = OH, R3 = H, R4 = OH
5 Rl CHO, R2 = H, R3 R4 = Me
6 Rl CH20H, R2 = C02H, R4 = Me
= OH, R3
1002 Rl CH20H, R2 = H, R3 = Me, R4 = C02H
1003 Rl CH2oAe, R2 = H, R3 = Me, R4 = C02H
0 CHO
1111
~
FIGURE 1. Structures of diterpenes reported from the Compositae.
220 2. Compound Names, Structures and Sources
OH
7
OH
R,
8 R1 = CHO, R2 = H, R3 = OH, R4 = OH
957 R1 = CH20H, R2 = OH, R3 = OH, R4 = H
1112 R1 = CH20H, R2 = R3 = OAe, R4 = OH
1113 R1 = CH20H, R2 = R3 = R4 = OAe
1114 R1 = CH20H, R2 = OAe, R3 = H, R4 = OR
1115 R1 = CH2oH, R2 = H, R3 = OAe, R4 = OH
OH
15 R1 = H, R2 = CH2oAe, R3 = CH20H
948 R1 = OH, R2 = CH20H, R3 = Me
OH
1116 R =H
1117 R = OH
FIGURE 1. (contd.)
0 OH
y~
OH
978
OH OH OH
y~
I (
OH
949
OH
979 R,
1004 R1 = R2 = OR
1005 Rl = R2 = OAe
OH
1095
FIGURE 1. (contd.)
J
C
OH
~
H~ OH
1096
OH
H
--
-
y~
I
OH COAC
1020
CHO OH
14
2. Geranylgeraniol
OH
y~ ~~R
I
!
"OH
11 R = OH
12 R = OAe
FIGURE 1. (contd.)
R,
13 Rl = OH, R2 = Me, R3 = H
954 Rl = H, R2 = C02H, R3 = H (lD,llE)
OH
I
HO
16
17 Rl CHO, R2 = H, R3 = Me, R4 = H
18 Rl CHO, R2 = OH, R3 = Me, R4 = H
19 Rl CH20Ae, R2 = H, R3 = C02H, R4 = H
1118 Rl CH20H, R2 = H, R3 = CH20H, R4 = OAe
20
FIGURE l. (contd.)
1119
,OH
21
22
CHO
.~ f\-OH
1120
r
CHO
3. Geranyllinalool
OH
FIGURE l. (contd.)
24 Rl = R2 = H, R3 = OH
25 Rl = R2 = H, R3 = OAe
26 Rl = H, R2 = OH, R3 = H
27 Rl = H, R2 = OAe, R3 = H
28 Rl = OH, R2 = R3 = H
29 Rl = OH, R2 = OAe, R3 = H
30 Rl = R2 = OAe, R3 = H
31 Rl = OH, R2 = H, R3 = OAe
1121 Rl = R2 = H, R3 = OAe
32
1122 (lO,ll-dihydro-homolog of 32)
OH
~
o
33
34
FIGURE 1. (contd.)
OH
35
o OH
HO ~~.
I
('
1123
OH
36
OH
OH
37 Rl = R2 = H
38 Rl = OH , R2 = H
39 Rl = H, R2 = OAe
4. Phytol
59
FIGURE 1. (contd.)
9 R = OH
10 R = OAc
o OH
980
OH
OH
981
OH
982
OH
OH
983
FIGURE l. (contd.)
OH
1094
40 Rl = OH, R2 = R3 = H
41 R1 = OAe, R2 = R3 = H
42 Rl = R2 = OH, R3 = H
43 R1 = OH, R2 = OAe, R3 = Ii
1124 Rl = OAe, R2 = H, R3 = Ae
6. Acanthoaustralane-6,1l-Epoxlde
OH
44 R = OAe
45 R = OH
FIGURE 1. (contd.)
7. I soacanthoaustra1ane
OH
R,
r
46 Rl = R2 = OH
47 Rl - OH , R2 = OAe
48 Rl = OAe, R2-- H
8. . 1-18
Gerany1geran~o , 8-Lactone
OH
r
I
~R
I
49 R = H
50 R = OAe
OH
51 R = OOH
S2 R = OH
FIGURE 1. (contd.)
53 R = OOH
54 R = OH
9. Oxepane
OH
55
R
HO~
56 R = OAc
1098 R = OH
OH
57
FIGURE 1. (contd.)
OH
1097
OH
1099
86. Me1canthane
1006
10. Mikanofurane
58
FIGURE 1. (contd.)
11. Centipedane
R3
~r R, R2
J
o
60 Rl C02H, R2 = Me, R3 = H
61 Rl R2 = CH2oH, R3 = H
1126 Rl R2 = Me, R3 = OH
1125 R = H
1127 R = OH
~
HOO~
1128
12. Geranylgeraniol-l,20-Lactone
y~
R
62 R = C02H
63 R = c02Me
FIGURE 1. (contd.)
o
o
1129
1130 R = H
1131 R = H (IO,IIE)
1132 R = Ac
OH
64
1133 R =H
1134 R = Ac
FIGURE 1. (contd.)
1135 R =H
1136 R = Ac
1137
65 R = CH20H
66 R = CHO
1138
FIGURE 1. (contd.)
68
69
70
71
72
FIGURE 1. (con/d.)
1101
14. Isocembrene
HO-4--(
73
HO
OH OH
74 R = OH
75 R = OAe
FIGURE 1. (contd.)

16. Normal-Labdane
79 Rl = H, R2 = CH20H
80 Rl = OH, R2 = CH20H
958 Rl = H, R2 = C02H (=121?)
H
OH
86 H
87 OH
81
FIGURE 1. (contd.)
H
~OH
1139
H
HO",
RO\\\
124 R= H
125 R = Mebut-2-0H
126 R = Ang
129
R, \\\
76 Rl R2 = H, R3 = CH20H
77 Rl OH, R2 = O~-Gal, R3 CH20H
111 Rl = R2 = H, R3 = C02H
FIGURE 1. (contd.)
1140 Rl = OH, R2 = a-OH

1141 Rl = OAe, R2 = a-OH
1142 Rl = OH, R2 = ~-OH
1143 R = H
1144 R = Ae
OH
1103
R,O",
78 Rl = H, R2 = H, R3 = CH20H
FIGURE 1. (contd.)
108 Rl = H, R2 = OAng, R3 = c02H

109 Rl = Ang, R2 = OH, R3 = c02H
OR,
82 Rl = R2 = H
83 Rl H, R2 = Ac (Acetylation product)
84 Rl R2 = Ac (Acetylation product)
o
~OH
85
88 Rl = R2 = R3 = H
89 Rl OH, R2 = R3 = H
90 Rl R2 = H, R3 = Ac
91 Rl = OH, R2 = H, R3 Ac
92 Rl = H, R2 = Ac, R3 H
93 Rl = OH, R2 = Pro, R3 Ac
FIGURE 1. (contd.)
H
OH
HO"\
995
..... COtH
959
R3 Rot
100 Rl = OAng, R2 = H, R3 = R4 = Me
116 Rl = H, R2 = OH, R3 = R4 = Me
101 Rl = R2 = H, R3 CH20Ang, R4 = Me
102 Rl = R2 = H, R3 CH2oTig, R4 = Me
103 Rl = a-OH, R2 = OAng, R3 = R4 = Me
1Ci4 Rl = a-OH, R2 = O-trans-Cinn, R3 = R4 = Me
105 Rl = a-OH, R2 = O-cis-Cinn, R3 = R4 = Me
106 Rl = a-OH, R2 OAng, R3 = R4 = Me
FIGURE 1. (contd.)
107 R1 = a-OAng, R2 = OH, R3 = R4 = Me

110 R1 = R2 = H, R3 = Me, R4 = C02H
o C~H
An90 III
97
H
CHO
977
112 R1 OTig, R2 = H, = Me
R3
113 R1 H, R2 = j3-0Ac, R3 = Me
114 Rl H, R2 = a-OH, R3 = Me
115 Rl H, R2 j3-0H, R3 = Me
130 Rl = R2 = H, R3 = C02H
FIGURE 1. (contd.)
(
-
o
// H
117
98 Rl OAng or OMebut-2-0H, R2 OAng or OMebut-2-0H,
R3 O-trans-Cinn
99 Rl OAng or OMebut-2-0H, R2 OAng or OMebut-2-0H,
R3 O-cis-Cinn
1024 R1 R2 = R3 = H
R3
R..
118 Rl R2 = H, R3 = C02H, R4 = Me
119 Rl H, R2 a-OH, R3 C02H, R4 Me (=9917)
120 Rl H, R2 = 13-0H, R3 C02H, R4 Me
FIGURE 1. (contd.)
122 Rl = R2 = H, R3 = C02H, {{4 = CH20Ang

123 Rl = R2 = H, R3 C02H, R4 = CH20Tig
127 Rl = OH, R2 = a-O-trans-Cinn, R3 = C02H, R4 = Me
128 Rl OH, R2 = a-O-cis-Cinn, R3 = C02H, R4 = Me
131 Rl = R2 = H, R3 = R4 = C02H
870 Rl = OSen, R2 = 13-0Ac, R3 = C02Me, R4 = Me
871 Rl = OH, R2 = H, R3 = CH20H, R4 = Me
872 Rl = OH, R2 = H, R3 = CH20Coum, R4 = Me
873 Rl = OH, R2 = H, R3 = CH203-Me-Coum, R4 = Me
874 Rl = OH, R2 = H, R3 = CH20-P-OH-Cinn, R4 = Me
R,
1145 Rl = H, R2 = OH
1146 Rl OH, R2 = H (=120)
121 (=9587)
R3 R4
132 Rl = R2 = H, R3 R4 = Me
FIGURE 1. (contd.)
133 R1 = a-OH, R2 = H, R3 R4 = Me
134 R1 ~-OH, R2 = H, R3 R4 = Me
135 R1 ~-OAe, R2 = H, R3 = R4 = Me
137 R1 = R2 = H, R3 = C02H, R4 = Me
138 Rl H, R2 = a-OAe, R3 = C02H, R4 = Me
1104 Rl R2 = H, R3 = Me, R4 C02Me
1147
H
HO \\\
991 R = C02H (=119? )

992 R = c02Me
993 R = CH20H
994 R = CH202-Mebut
o
136
FIGURE 1. (contd.)
Rl
139 Rl = R2 = H
140 Rl H, R2 OH
1021 Rl H, R2 = OAe
1023 Rl = R2 = OH
R2
141 Rl R2 = H, R3 = OH, R4 = Me
142 Rl H, R2 = a-OH, R3 = OH, R4 = Me
143 Rl H, R2 = a-OAng, R3 = OH, R4 = Me
144 R1 H, R2 ~-OH, R3 = H, R4 Me
145 Rl R2 = H, R3 = OAe, R4 = Me
146 Rl = H, R2 ~-OH, R3 = OH, R4 = Me
147 Rl = H, R2 ~-OH, R3 = H, R4 = CH20H
148 Rl = H, R2 ~-OH, R3 = OAe, R4 = Me
149 Rl = OAe, R2 R3 = H, R4 CH20Arae
150 Rl = OAe, R2 R3 = H, R4 CH20Coum
151 Rl = OAe, R2 R3 = H, R4 CH2o-eis-coum
1022 Rl = H, R2 = a-OH, R3 = OAe, R4 = Me
FIGURE 1. (contd.)
l
X~
~OH
152
OR,
94 Rl = R2 = H
95 Rl = H, R2 = Ac (Acetylation product)
96 Rl = R2 = Ac (Acetylation product)
OH
153 R = a-OAng
1102 R =H
FIGURE 1. (contd.)
OH
996 OH
HO
154
1105 R = H
1106 R = OH
OH
95 R = Tig
96 R =H
FIGURE 1. (contd.)
R, 0
f.E{1
OH O~
1148 Rl CHO, R2 = Ac
1149 Rl c02Me, R2 Ac
OH
1150 Rl c02Me, R2
1107
155 Rl = R2 = R3 = R4 = H
156 Rl = OH, R2 = OAe, R3 r3-0-0H, R4 =H
157 Rl = OH, R2 = OAe, R3 = a-O-OH, R4 =H
1151 Rl = R2 = R3 = H, R4 = OAe
FIGURE 1. (contd.)
1152
o
158
R2
o 0
H
R,
159 Rl = H, R2 = CH20H, R3 = C02H
160 Rl = 02-Mebut, R2 = C02H, R3 = Me
161 Rl = Oi-But, R2 = c02H, R3 = Me
162 Rl = Oi-Val, R2 = c02H, R3 = Me
163
FIGURE 1. (contd.)
17. Grindelane
OH
165 R = a-OH
1036 R = J3-0H
166 o
R2
RJ
167 Rl = R2 = R3 = H, R4 = Me
168 Rl = OH, R2 = R3 = H, R4 = Me
169 Rl = H, R2 = J3-0H, R3 = H, R4 Me
170 Rl = R2 H, R3 = a-OH, R4 = Me
171 Rl = R2 H, R3 = a-OCHO, R4 = Me
172 Rl = R2 H, R3 J3-0H, R4 = Me
173 Rl = R2 R3 = H, R4 = CH20H
FIGURE 1. (contd.)
174 Rl R2 R3 H, R4 CH20Ac
175 Rl R2 R3 H, R4 CH20Pro
176 Rl R2 R3 H, R4 CH20i-But
177 Rl R2 R3 H, R4 CH20i-Val
178 Rl R2 R3 H, R4 CH202-Mebut
179 Rl R2 R3 H, R4 CH20Me
1035 Rl H, R2 = a-OH, R3 = H, R4 Me
yO
OR;,
R, R2
180 Rl Me, R2 CH20H, R3 =H
181 Rl Me, R2 CH20Ac, R3 = H
182 Rl Me, R2 CH2oi-Val, R3 H
183 Rl Me, R2 CH2oi-But, R3 H
184 Rl Me, R2 CH202-Mebut, R3 H
185 Rl Me, R2 CH20Succ, R3 =H

186 Rl Me, R2 CHO, R3 =H
187 Rl Me, R2 C02H, R3 = H
R2 = Me, R3 = H
:yO
188 Rl CH20H,
1153 Rl Me, R2 = c02H, R3 = Me
OH
189 R Me
190 R CH20Ac
FIGURE 1. (contd.)
fO
I
OH
191
192
o
193
II
H
o
194
FIGURE 1. (contd.)
955
a
a-Arab
1060 a
a
H IIa
956
o
OH
0, ,0 "- J
~OH
OH
1187
FIGURE 1. (contd.)
18. Normal-Labdane-8,13-Epoxide
R,
-
H
R2
RJ R.
272 Rl R2 H, R3 R4 = Me
195 Rl = R2 H, R3 Me, R4 CH20H
196 Rl = R2 = H, R3 Me, R4 CH20Ae
197 Rl OH, R2 H, R3 Me, R4 CH20H
198 Rl = OH, R2 H, R3 = Me, R4 CH20Ae
199 Rl = OAe, R2 = H, R3 Me, R4 = CH20Ae
200 Rl H, R2 OAe, R3 = R4 = Me
201 Rl = H, R2 OH, R3 = CH20Benz, R4 Me
\\\\~
CHO
964
273 R Me
202 R CHZOH
FIGURE 1. (contd.)
19. Norma1-Labdane-8,12-Epoxide
---
H
203 Rl R2 = CH20H
204 Rl CH20H, R2 = CH20Ac
205 Rl R2 = CH20Ac
206 Rl CH20H, R2 CHO
207 Rl R2 = CHO
210 Rl CH20H, R2 = Me
211 Rl C02H, R2 = Me
;:CHO
\ CHO
212 o CHO
:;r:CH20AC
,0
\,\"
H
213
FIGURE 1. (contd.)
HO
1rOH ....
208
HO
~OH ~
209
R2
164 Rl Me, R2 = C02H
965 Rl CH2oH, R2 = Me
966 Rl = CHO, R2 = Me
FIGURE 1. (contd.)
OH
214
22. Norma1-Labdane Spiroketa1

o
R,O"
AngO'"
215 Rl Ang, R2
)8
H
0
216 Rl Ang, R2 a-CH
217 Rl Ang, R2 i3-0H
HO '"
AngO'"
218
FIGURE 1. (contd.)
88. Normal-Labdane-15,12-Lactone ,
o
H
HO
\\ \
, " 'OAe
, H
938
219 OH
Normal-Labdane, 3,4-Seco-
~
o
220
OH
,
, H
y
223 o
FIGURE 1. (contd.)
89. Grindelane, 19-Hor-
221 R =H
222 R = CHO
1154
26. Grindelane, 8,11-Bis-Hor-8,9-Seco-
224
FIGURE 1. (contd.)
27. Normal-Labdane-20,12-Lactone, 5,10-Seco-
~Ang
230 (Reaction product)
225 R =H
226 R = Ang
227 R = i-But
228 R = 2-Mebut
229 R = i-Val
FIGURE l. (contd.)
100. Normal-Labdane, 14,15-Bisnor-
1155 R1 = R2 = H
1157 R1 = R2 = OH
1158 R1 = OAc, R2 = OH
1159 R1 = OH, R2 = OAc
1160 R1 = H, R2 = OH
101. Normal-Labdane, 13,14,15,16-Tetranor-
1156
87. Hexanorlabdane
OH
941
FIGURE 1. (contd.)
Figure 1. Structures of D'Iterpenes 263
28. Relhaniane
231
~OH
232
233
234
FIGURE 1. (contd.)
235
29. trans- Normal-Clerodane
(No proven structures of this skeletal type)
255 R C02H (Revised to 9a-Me; = 573)

256 R C02Me (Revised to 9a-Me; = 573 methyl derivative)
R,
238 Rl = Me, R2 CH20H (= 241)

FIGURE 1. (contd.)
239 Rl = Me, R2 = C02H

240 Rl = Me, RZ = CHO (= 1062)
241 Rl = Me, R2 = CHZOH (= 1064)
242 Rl = R2 = CH20H
243 Rl = R2 = CHO (= 1063)
244 Rl = CH2oAng, R2 = COZH
1065 Rl = CH20H, R2 = Me
R2
253 Rl = R2 = H, R3 = CHZOH
258 Rl = H, R2 = OAng, R3 = Me
259 Rl = H, RZ = OTig, R3 = Me
263 Rl = OH, RZ = OAng, R3 = Me
264 Rl = OH, RZ = OTig, R3 = Me
545 Rl H, R2 OH, R3 == Me
546 Rl = H, R2 OAe, R3 == Me
0
R"II
551 Rl = OH, RZ =H
552 Rl = H, RZ = OAng
FIGURE 1. (contd.)
-
"'OH
254
257
R
260 R = [3-0Ang
553 R = [3-0Ac
988 R = [3-0Tig
556 R =H
0
261
FIGURE 1. (contd.)
0
262 R= H
,/J
265 R = OH
O
,
HO
OR
" era
266 R = Ang
267 R = Tig
o
OR
268 R = Ang
269 R = Tig
246
FIGURE 1. (contd.)
247
CI \"
HO
270
557
OH
OAc
1025
FIGURE 1. (contd.)
1066
1067
1068 (= 2477)
R2
1083 Rl = OH, R2 = CH20H, R3 = Me
1084 Rl = H, R2 = R3 = CH20H
1091 Rl = H, R2 = Me, R3 =C02Arab
FIGURE 1. (contd.)
1085
1086
1087
o
1088
FIGURE 1. (contd.)
o
o
1089
-0
HO ",
HO
1090
0
HO 0
1092
C)=o
H
OH
947
FIGURE 1. (contd.)
72. Chrysolane
271
III. Normal Tricarbocyclics and Derivatives

32. Sandaracopimaranes (Normal-Pimaranes)
274 Rl R2 = R3 = H
927 Rl H, R2 = OH, R3 = H
928 Rl = R2 = OH, R3 H
929 Rl OAe, R2 = OH, R3 H
930 Rl OH, R2 OAe, R3 = H
931 Rl OH, R2 H, R3 = OH
932 Rl = OAe, R2 = H, R3 = OAe
933 Rl OH, R2 = OAe, R3 OH
934 Rl OAe, R2 OH, R3 OAe
935 Rl R2 = R3 OAe
FIGURE 1. (contd.)
936
937
R,
R2
275 Rl H, R2 Me
301 Rl H, R2 C02H
303 Rl OAc, R2 R3
FiGURE 1. (contd.)
277 Rl = OH, R2 = R3 = H, R4 = Me
278 Rl OAe, R2 = R3 = H, R4 = Me
279 Rl H, R2 OH, R3 H, R4 Me
280 Rl H, R2 OSen, R3 = Me
H, R4
281 Rl H, R2 OTig, R3 = H, R4 = Me
282 Rl H, R2 H, R3 = OAe, R4 = Me
284 Rl = R2 = H, R3 OAe, R4 = Me
285 Rl = R2 R3 = H, R4 = CH20H
288 Rl = H, R2 = R3 = OH, R4 = Me
289 Rl = H, R2 = OAe, R3 = OH, R4 = Me
290 Rl = H, R2 = OSen, R3 = OH, R4 = Me
291 Rl = H, R2 = OTig, R3 = OH, R4 = Me
292 Rl = H, R2 = OH, R3 = OAe, R4 = Me
293 Rl = H, R2 = OH, R3 = OCoum, R4 = Me
294 Rl = H, R2 R3 = OAe, R4 = Me
298 Rl R2 = OH, R3 = H, R4 = Me
299 Rl = OAe, R2 = OH, R3 = H, R4 = Me
283 R H
296 R OH
297 R = OAe
FIGURE 1. (contd.)
286
287
295
300 R= H
302 R = OAe
FIGURE 1. (contd.)
HO
807
921
IIII~
'\ OH
OH
OH, R2 = H
OH
306 Ri OH, R2 = H, R) = CH20H (Revised to rosane)
307 Ri R2 = OH, R) = Me (Revised to rosane)
FIGURE 1. (contd.)
891
OH
HO
308
~-OG1u, R2 = Me (Probably ent-pimarane; = 593?)

923 Rl a-OH, R2 = CH20H (Probably ent-pimarane; = 944?)
FIGURE 1. (con/d.)
34. Cassane
HO '"
310 R = H
311 R = OH
HO",
312
35. Rosane
R,O
313 Rl = H, RZ = Me
314 Rl = H, RZ = CHZOH
1161 Rl = Ac, RZ = CHZOAc
1162 Rl = Ac, R2 CH20H
FIGURE 1. (contd.)
315
R, \\ \
R2
881 Rl = H, R2 = Me
882 Rl = H, R2 = CH20H
883 Rl = H, R2 = CH20Ac
884 Rl = R2 = Me
885 Rl = H, R2 = CH20Tig
886 Rl = OH, R2 = CH20H
R,O \\\
R2 0
887 Rl = R2 = H
888 Rl Ac, R2 =H
889 Rl = H, R2 = Ac
FIGURE 1. (contd.)
890
36. Sandaracopimarane, 19-Nor-13-Epi
OH
OH
309
37. Normal-Abietane
316 R1 = OAc, R2 H (316-318 probable artifacts; dehydration

products ?)
317 R1 = H, R2 = OH
FIGURE 1. (contd.)
316 Rl = OAe, R2 = H (Possible dehydration precursor)
o
318
HO
319
OMe
320
FIGURE 1. (contd.)
OH
321
OH
322
OH
323
FIGURE 1. (contd.)
OH
324
1072 Rl = OH, R2 = Sen

1073 Rl = OSen, R2 =H
1074 Rl = R2 = H
OH
1163
FIGURE 1. (contd.)
94. stevisalane
OH
~
,,\\'
OH
1026
73. Normal-Stachane
325 (Probable ent-stachane; = 7741)

38. ent-Lab<iane
R.
R, "I
326 Rl = R2 = R3 H, R4 CH2oH, RS = Me
327 Rl = R2 = R3 H, R4 CH20bern, RS = Me
FIGURE 1. (contd.)
848 Rl = OH, R2 = R3 = H, R4 = CH2oH, RS = Me

328 Rl = R2 = H, R3 = OAe, R4 = CH2oH, RS = Me
844 Rl = H, R2 = OAng, R3 = H, R4 = RS = CH20H
329 Rl = R2 = R3 = H, R4 = CH2oH, RS = c02H
330 Rl = R2 = R3 = H, R4 = CH20Ae, RS = c02H
331 Rl = OH, R2 = R3 = H, R4 = CHO, RS = Me
335 Rl = R2 = R3 = H, R4 = c02H, RS = Me (= 1040)
1014 Rl = H, R2 = OAe, R3 = H, R4 = CH20H, RS = CH20Tig
1041 Rl = R2 = R3 = H, R4 = c02H, RS = CH20H
1164 Rl = R2 = R3 = H, R4 = RS = C02H
OH
1165 Rl = R2 = R3 = H
1166 Rl = H, R2 = Ae, R3 =H
1167 Rl = Ac, R2 = R3 = H
1168 Rl = H, R2 = Ae, R3 = OH
OH
OH
CH;s~ 0--""""0
I~OH
AcO OH
AngO ",
1169
FIGURE 1. (contd.)
OH
1170
OH
HO r--O~O
~OH
OH
1171
O,/O~
"'-T---L- OHOH
OH
1172
849 R = CHZOH
333 R = eHO
FIGURE 1. (contd.)
R, 'I,
332 Rl = OH, R2 = R3 = H, R4 = CHO

336 Rl = R2 = R3 = H, R4 = C02H
337 Rl = H, R2 = OH, R3 = H, R4 = C02H
338 Rl = H, R2 = R3 = OH, R4 = C02H
~OH
1173
CHO
334
FIGURE 1. (contd.)
R, \"
339 Rl = OH, R2 = H, R3 = CHO

340 Rl = OH, R2 = CHO, R3 = H
343 Rl = OH, R2 = CHO, R3 = OH
344 Rl = H, R2 = H, R3 = C02H
o
341 R1 = H, R2 = CHO
342 Rl = CHO, R2 =H
345
FIGURE 1. (contd.)
346
Obern
347
R
348 R = CH20H
349 R = CHO
~OH
~ ~ \
HO ~
OH
1174
FIGURE 1. (contd.)
CHO
350
351 R1 = H, R2 = OH, R3 = CH20H

355 R1 = OAng, R2 = H, R3 = C02H (13,14 Z or E)
~OH
o
352
OAc
AcO"\
353
FIGURE 1. (contd.)
354
356
i-VoiO III
358
R1 III
357 Rl = OH, R2 = CH20H

857 Rl = OH, R2 = C02H
FIGURE 1. (contd.)
858 Rl =OAng, R2 =C02H

859 Rl = OTig, R2 = C02H
860 Rl = 02-Mebut, R2 = c02H
R
o
359 R = CH20H
861 R = C02H
RO",
862 R = OAn;
863 R =02-Mebut
R,
360 Rl = H, R2 = CH2oMe, R3 = Me
361 Rl = ~-OAnq, R2 = R3 = Me
FIGURE 1. (contd.)
1046 R1 = H, R2 = CH20H, R) = Me
1047 Rl = H, R2 = CH20Ac, R) = Me
1048 Rl = H, R2 = CHO, R) = Me
1049 Rl = a-OH, R2 = CH20H, R) = Me
1050 Rl = a-OH, R2 = CH20Ac, R) = Me
1051 Rl = a-OH, R2 = CHO, R) = Me
1052 Rl = H, R2 = C02H, R) = Me
1053 Rl = H, R2 = CH20Ac, R) = CH20H
1179 Rl = OH, R2 = CH20Me, R) = Me
HO \\\
1175 R = CH20H
1176 R = CH20AC
1177 R = CHO
1178 R = CH20Me
362 Rl = R2 = R3 = CH20H
363 Rl = R2 = CH20Ac, R) = Me
FIGURE 1. (contd.)
364 Rl = R2 = R) = CH20AC
366 Rl = C02H, R2 = CH20H, R) = Me
361 Rl = C02H, R2 = R) = CH20H
369 Rl = C02H, R2 = CH20H, R) = CHO
310 Rl = C02H, R2 = CH20AC, R) = CH20H
1180 Rl = C02H, R2 = CH20H, R) = CH20Me
365
OH
368
FIGURE 1. (contd.)
R,
371 Rl = H, R2 = CH20Ac
372 Rl = a-OH, R2 = CH20Ac
373 Rl = j3-0H, R2 = CH20Ac
o
314 R = CH20Ac
315 R = CHO
316 R = CH20H o
311 R = CH20Ac
318 R = CH20Me
FIGURE 1. (contd.)
379 Rl = OH, R2 = H, R3 = Me
380 Rl = H, R2 = Ac, R3 = CHO
381 Rl = H, R2 = Ac, R3 = C02H
OH
382
383
FIGURE 1. (contd.)
384
385
1181 Rl = R2 = H, R3 = OH
1182 Rl = H, R2 = OAng, R3 = H
1183 Rl = Glu, R2 = OAng, R3 = H
1184 Rl = H, R2 = OAng, R3 = OH
FIGURE 1. (contd.)
386 R1 = R2 = H
387 R1 = OH, R2 = H
388 R1 = H, R2 = a-OH
389 R1 = H, R2 ~-OH
390 R1 = R2 = OH
391 R1 = OH, R2 = a-OH
392 R1 = OH, R2 = ~-OH
0
393 R = H
394 R = OH
395 R = a-OH
396 R = ~-OH
FIGURE 1. (contd.)
397 R1 = OH, R2 = Me
843 R1 = H, R2 = c02H
R1
398 R1 = R2 = H
399 Rl = OH, R2 = ~-OH
400 Rl = OH, R2 = a-OH
401 R1 = R2 = H, R3 = OH, R4 = RS = Me
402 R1 = R2 = H, R3 = OAe, R4 = RS = Me
403 R1 = R2 = R3 = H, R4 = Me, RS = CH20H
FIGURE 1. (contd.)
404 R1 = H, R2 = OH, R3 = H, R4 = Me, RS = CH20H

839 R1 = R2 = R3 = H, R4 = Me, RS = C02H
840 R1 = OH, R2 = R3 = H, R4 = Me, RS = c02H
841 Rl = R2 = R3 = H, R4 = RS = CH20H
842 R1 = OH, R2 = R3 = H, R4 = CH20H, RS = Me
974 R1 = OAng, R2 = R3 = H, R4 = CH20H, RS = Me
975 R1 = OH, R2 = R3 = H, R4 = CH2oAng, RS = Me
830 R1 = R2 = R3 = H, R4 = C02H, RS = Me
831 Rl = OH, R2 = R3 = H, R4 = C02H, RS = Me
832 Rl = OAng, R2 = R3 = H, R4 = C02H, RS = Me
833 Rl = 02-Mebut, R2 = R3 = H, R4 = C02H, RS = Me
834 Rl = Oi-But, R2 = R3 = H, R4 = C02H, RS = Me
83S Rl = R2 = R3 = H, R4 = C02H, RS = CH20H
~
o
836
837
FIGURE 1. (contd.)
838
40S OH
406 R = H
413 R = OH o
407 R= H
412 R = OH
FIGURE 1. (contd.)
408 R1 = OAc, R2 = CH20H

409 R1 = OAc, R2 = CH20Ac
410 R1 = OH, R2 = CHO (Saponification product)
411 R1 = OAc, R2 = CHO
414 R1 = CHZOH, R2 = Me
415 R1 = Me, RZ = C02H
AngO \\\
416
FIGURE 1. (contd.)
o
R
417 R = a-OH
418 R = 13-0H
OH
421
R1 1/,
R2
422 R1 = H, R2 = Me
423 Rl = H, R2 = CHO
424 Rl = H, R2 = C02H
426 Rl = OH, R2 = C02H
FIGURE 1. (contd.)
425
427
Rl
428 Rl = R2 = R3 = OH
429 Rl = OAe, R2 = R3 = OH
808 Rl = OAng, R2 = OAe, R3 = ~-OH
FIGURE 1. (contd.)
R2
\\\
RJ R.
430 R1 = R2 = H, R3 = R4 = Me
431 R1 = R2 = H, R3 = Me, R4 = CH20H
432 R1 = H, R2 = OH, R3 = Me, R4 = CH20H
433 R1 = R2 = H, R3 CH2oH, R4 = Me
434 R1 R2 H, R3 = R4 CH20H
435 R1 = OAe, R2 = H, R3 = C02H, R4 = Me
1185 R1 R2 = H, R3 = R4 = CH20Ae
R,
R4 R2
436 Rl = OH, R2 = R3 = H, R4 Me
809 R1 = H, R2 = R3 = OH, R4 = Me
810 R1 = H, R2 = OAe, R3 = OH, R4 = Me
811 Rl H, R2 = OAng, R3 = OAe, R4 = Me
1015 R1 = R2 = R3 = H, R4 = CH20H
\\\
HO
1186
FIGURE 1. (contd.)
437
438
439
440
FIGURE 1. (contd.)
OH
442 R =H
443 R = ~-OH
444 R = a-OH
445 R = ~-OSucc
OH
446
OH
447 R =H
448 R = OH (Revised to normal-labdane; = 1106?)
FIGURE 1. (contd.)
OH
o
449 (Revised to normal-labdane; = 11077)
OH
450
o
460
~OSen
OH ( \
""
-'> 0
: "
461
FIGURE 1. (con/d.)
1012 R = OAe
1013 R = OH
OH
HO
1016
1017 R = CH20H
1018 R = CHO
1019 R = C02H
FIGURE 1. (con/d.)
1037 R1 = H, R2 = OAng
1038 Rl = OH, R2 = OAng
HO
1188
1039
1189 Rl = C02H, R2 = H, R3 = OH, R4 =H

FIGURE 1. (contd.)
1190 Rl = c02H, R2 = H, R3 = OAng, R4 =H

1191 Rl = CH20H, R2 = OH, R3 = OAng, R4 = OH
1192 R = a.-OAng
1193 R = fl-OH
1194 R =H
1195 R = OH
1196 R = C02H
1197 R = CH20H
FIGURE 1. (con/d.)
R2 R,
1042 Rl = OH, R2 = CHO
1043 Rl = O-i-Val, R2 = C02H
1044
HO
1045
39. ~-Labdane-19,6-Lactone
C~H
462
FIGURE 1. (contd.)
40. ~-Labdane-8,13-Epoxide-15,16-Hemiacetal
463 R =H
464 R = Ac
97. ent-Labdane Dimer
419 R = a-H
420 R = I3-H
FIGURE 1. (contd.)
98. ent-Manayl Oxide, 13-Epi-
R, ",
451 R1 = H, R2 = Me
452 R1 = OH, R2 = Me
455 R1 = H, R2 = CH20H
1198 R1 = OAe, R2 = Me
1199 R1 = OH, R2 = CH20Cinn
1200 R1 = OH, R2 CH20H
453
454 R = Me
456 R = CH20H
FIGURE 1. (contd.)
457
99. ent-Manoyl Oxide
458 R =H
459 R = OH
465
FIGURE l. (contd.)
466 Rl = H, R2 = CH20Ac
467 Rl = OH, R2 = Me
1201 Rl = OH, R2 = Me (6,7-dlhydro)
o
468
1202 (6,7-dlhydro)
42. ~-Labdane, 1S-Nor-

CHO
469
FIGURE 1. (contd.)
470
CH3~O-T'O
I~OH
AcO OH
AngO \\\
1203
471 Rl = CHO, R2 = Me
472 Rl = C02H, R2 = CH20H
FIGURE 1. (contd.)
45. ent-Labdane, 7,8-Seco-
I, 0
';~H - c02H
I"
473
HO I"
HO ,\'
828 (Structure revised; = 1206)
RO / ,
HO ,\'
o
1205 R = Ac
1206 R = H
RO I"
o
829 R = H
1207 R = Ac
FIGURE 1. (contd.)
HO
1059
1208 (Illustrated in report as l3,l4-dihydro-homolog of 1059,
but text indicates that 1208 is identical to 1059.)
OH
1209 X =0
1210 X = a-OH,H
1211
FIGURE l. (contd.)
11111
HO\\\
1212
11111
HO \\\
1213
11111
HO\\'
1214
102. ent-Friedolabdane, 3,4-seco-
~
/"
'I 11111
FIGURE 1. (contd.)
1216 R1 = OH, R2 = H
1217 R1 = R2 = OH
1218 R1 = OMe, R2 = OH
J: '" " 11111
o 0
1219
1220
103. ent-Friedolabdane, rearranged-
o
1221
FIGURE 1. (contd.)
OH
H
1222
R1
248 Rl = c02H, R2 = Me (= 512 = 2501)
911 Rl = c02H, R2 = CH20AC

1070 Rl = c02H, R2 = CH20H
R1
475 Rl = R2 = H, R3 = CH2oH, R4 = Me
476 Rl = R2 = H, R3 = R4 = CH20H
1010 Rl = R2 = H, R3 = CH20Arac, R4 = CH20H
1011 Rl = R2 = H, R3 = CH20Behen, R4 = CH20H
FIGURE 1. (contd.)
495 Rl = R2 = H, R3 = C02Me, R4 = Me
496 Rl = 13-0Ac, R2 = H, R3 = C02Me, R4 = Me
497 Rl = 13-0Ang, R2 = H, R3 = C02Me, R4 = Me
498 Rl = a-OAng, R2 = H, R3 = c02H, R4 = Me
499 Rl = a-OTig, R2 = H, R3 = C02H, R4 = Me
500 Rl = H, R2 = OAc, R3 = C02H, R4 = Me
535 Rl = R2 = H, R3 = CHO, R4 = CH20H
537 Rl = R2 = H, R3 = CHO, R4 = C02H
OH
H
-
OH
1223
OR,
1224 Rl = R2 = H
1225 Rl = Ac, R2 = OH
1226
FIGURE 1. (contd.)
OAe
1227
OH
236
OAe
R,O '"
477 Rl = H, R2 = Me
478 Rl = H, R2 = CH20H
1228 Rl = Ac, R2 = CH20H
OH
479 R= H
R
480 R = OAng
FIGURE 1. (contd.)
R4
481 Rl = H, R2 R3 == CH2oH, R4 = Me
482 Rl H, R2 = CH20Arae, R3 = CH2oH, R4 = Me
483 Rl H, R2 = CH20Behen, R3 = CH20H, R4 = Me
484 Rl = H, R2 =CH20H, R3 = Me, R4 = CH20Suee
486 Rl H, R2 = CH20H, R3 = CHO, R4 = Me
488 Rl OH, R2 CH2oH, R3 CH2oAe, R4 = CH20H
489 Rl = OH, R2 = CH2oH, R3 = CH2oPhe-Ae, R4 = CH20H
490 Rl = OH, R2 = CH2oH, R3 = CH20Phe-Ae, R4 CHO
491 Rl = OH, R2 = CH2oH, R3 = CH2oAe, R4 = CHO
492 Rl = H, R2 CHO, R3 = CH20H, R4 = Me
503 Rl = H, R2 = C02H, R3 = R4 = Me
504 Rl H, R2 C02H, R) = Me, R4 = CH20Ae
OAc
1229 R =H
1230 R = OAe
FIGURE 1. (contd.)
OH
HO",
485
R,
487 Rl = CH20H, R2 = Ae
522 Rl = c02H, R2 = Phe-Ac
493 Rl = H, R2 = C02H, R3 = Me
494 Rl = OAe, R2 = c02H, R3 = Me
534 Rl = H, R2 = CHO, R3 = CH20H
536 Rl = H, R2 = CHO, R3 = C02H
FIGURE 1. (contd.)
HO",
HO III
962
501 R = Ac
502 R = Phe-Ac
961
505
FIGURE 1. (contd.)
506
R3
507 Rl = H, R2 = R3 = R4 = Me
508 Rl = H, R2 = Me, R3 = CH2oMal,= Me R4
509 Rl OH, R2 = Me, R3 = CH20H, R4 = Me
510 Rl = H, R2 = Me, R3 CH2oMal, R4 = CH20AC
846 Rl H, R2 = Me, R3 = R4 = CH20H
511 Rl H, R2 = Me, R3 c02H, R4 = Me (= 245? 249?)
967 Rl H, R2 CHO, R3 = R4 = Me
518 Rl H, R2 = Me, R3 c02H, R4 CH20H (=1033)
900 Rl = H, R2 Me, R3 = C02H, R4 = CH20AC
901 Rl = H, R2 = Me, R3 = C02H, R4 = CH20Me
902 R1 H, R2 = Me, R3 c02H, R4 CH20Ang
903 Rl = H, R2 = Me, R3 c02H, R4 CH20i-Val
904 Rl = H, R2 = Me, R3 = c02H, R4 CHO
1231 Rl = H, R2 = Me, R3 = CH20H, R4 = CH20Mal
1232 Rl H, R2 = Me, R3 CH20H, R4 Me
1233 Rl = H, R2 = Me, R3 R4 = CH20Ac
FIGURE 1. (contd.)
953 Rl = H, RZ = 02-Mebut, R3 = C02H, R4 = Me

513 Rl = a-OH, R2 = H, R3 = C02H, R4 = Me
519 Rl = ~-OH, R2 = H, R3 = C02H, R4 = CH20H
1034 Rl = ~-OH, R2 = H, R3 = C02H, R4 = CH20H (=519)
HO"\
R
514 R = CH20i-Val
515 R = CH202-Mebut
516 R = CH20Ang
524
FIGURE 1. (contd.)
R, H
520 R1 = R2 = R3 = H
521 R1 = OH, R2 = R3 = H
950 R1 = R2 = H, R3 = OH
951 R1 = H, R2 = R3 = OH
1234 R = H
1235 R = OH
A-- -O
o
523
FIGURE 1. (contd.)
865
R2
538 Rl = H, R2 = CH20H
539 Rl = Ac, R2 = CH20H
540 Rl = H, R2 = CHO
541 Rl = Ac, R2 = CHO
542
FIGURE 1. (contd.)
o
R, '"
543 R1 = R2 = H, R3 = R4 = Me
544 R1 = OH, R2 = H, R3 = R4 = Me
864 R1 = H, R2 = OH, R3 = R4 = Me
550 R1 = R2 = H, R3 = CH20H, R4 = Me
558 R1 = R2 = H, R3 = C02H, R4 = Me
909 R1 = H, R2 = a-OH, R3 = C02H, R4 = CH20H
910 R1 = H, R2 = 13-0H, R3 = C02H, R4 = CH20H
1236 R1 = H, R2 = OMe, R3 = CH20Ae, R4 = Me
559 R1 = OH, R2 = a, R3 = H
560 R1 = H, R2 :: OH, R3 = H
1237 R1 = R2 = H, R3 = 08
1238 R1 = R2 = H, R3 = OAe
FIGURE 1. (contd.)
561
562 R = OH
563 R= H
564 Rl = H, R2 = Me
565 Rl = OH, R2 = Me
963 Rl = OMe, R2 = CH20Ac
FIGURE 1. (contd.)
R,
566 Rl = H, R2 = R3 = Me, R4 = CHO
90S Rl = a.-OH, R2 = c02H, R3 = CH20H, R4 = Me
906 Rl = ~-OH, R2 = C02H, R3 = CH20H, R4 = Me
1240 Rl = H, R2 = CH20Ac, R3 = R4 = Me
907
908
567
FIGURE 1. (contd.)
568
H
569
1239 Rl OAe, R2 = Me
1241 Rl OH, R2 Me C0 2 H
1242 Rl OH, R2 CH20H
1243 Rl OAe, R2 = CH20Ae
i-But, R, Ae
FIGURE 1. (con/d.)
1028 Rl = Anq, R2 = Ac
1029 Rl = R2 = Ac
1030
O-i-8ut
1031
1033
1071 R = e02H
1076 R = Me
FIGURE 1. (contd.)
CHO
1075
CHO
1077
CHO
1078
CHO
1079
FIGURE 1. (contd.)
1080
1081
o
,\'
HO
HO
1082
570
FIGURE 1. (contd.)
525
526
o
\\\\\~o
527 Rl = R2 = H
1069 Rl = OH, R2 = H
FIGURE 1. (contd.)
1257 R1 = OAc, R2 =H
1258 R1 = H, R2 = OH
528
969
970
FIGURE 1. (contd.)
o
-:....
... -
,r0 =
= / OAng
971
o
972
~-;
-= 0/
Or-
973
FIGURE 1. (contd.)
R2
529 Rl R2 =H
530 Rl H, R2 OAng
968 Rl OAng, R2 H
532 Rl OSen, R2 H
l~o
533 Rl 02-Mebut, R2 H
.,'"
0
R,O", 11111
RZO ,.,
531 Rl = Ang, R2 = Sen

trans-ent-C1erodane DiJDer
H
,
O0
o~~
\O~ =
H
""
1244 R Mal
1245 R Succ
FIGURE 1. (contd.)
47. Printziane
HO
o
571
~
o
HO
o
572
~
o
HO
o
913 R =H
914 R = Me
HO
o
915
FIGURE 1. (contd.)
o
916
76. conyscabrane
917
~
o
OH
919
918
FIGURE 1. (contd.)
920
48. ent-Clerodane, 5,10-Seco-

R,
573 Rl R2 = H
912 Rl H, R2 = OAe
952 Rl 02-Mebut, R2 H
985 o
986
FIGURE 1. (contd.)
987
96. ~-ent-Clerodane, 17-Hor-
OH
106l
49. trans-ent-Clerodane, 13,14,15,16-Tetra-Hor-
574 Rl = R2 = H, R3 = R4 = CH20H
575 Rl = R2 = H, R3 = C02H, R4 = CH20H
1032 Rl = R2 = OH, R3 = C02H, R4 = Me
FIGURE 1. (contd.)
1093
Undetermined
OH
237
R,
R2
578 R1 = H, R2 Me
579 R1 H, R2 CH20H
580 R1 H, R2 CH20Ac
581 R1 OH, R2 CH20H
582 Rl = OH, R2 CH20Ac
FIGURE 1. (contd.)
576 R = C02H R
577 R = C02Me
583
o
584 R =H
585 R = OH
R
1055 R = CH20AC
1056 R = CH20H
FIGURE 1. (contd.)
1057 Rl = CH20H, R2 = Me
1058 Rl = Me, R2 = CH20H
1246
[YO
82. Solidagonane
OH
960
FIGURE 1. (contd.)
VI. ent-Tricarbocyclics and Derivatives

51. ~-Labdane, Cyclopropyl-
OH
586
77. Gutierreziane
845
52. ~-Pimarane
587 Rl = R2 = H
588 Rl = OH, R2 = OAe
FIGURE 1. (contd.)
II~
I" S OH
HO R
589 R = OH
595 R = 13-0H
590 Rl = H, R2 = Me, R3 = C02H

1247 Rl = OH, R2 = Me, R3 = CH20H
1248 Rl = OH, R2 = CH20H, R3 = Me
820
FIGURE 1. (contd.)
821 R = C02H
1249 R = CH20H
823 Rl = OAe, R2 = C02H

1250 Rl H, R2 = CH20H
599 Rl CH20H, R2 = Me, R3 = H
600 R1 C02H, R2 = Me, R3 = H
1251 R1 = Me, = CH20H, R3 = H

R2
1252 Rl = Me, R2 = CH20Mal, R3 = H
1253 Rl CH2oMal, R2 = Me, R3 = H
1254 Rl CH20H, R2 = Me, R3 = OH
FIGURE 1. (contd.)
III ( '
II OH
h
OH'
R2
591 Rl = OH, R2 = H, R3 = R4 = Me
592 Rl = OGlu, R2 = H, R3 = R4 = Me
593 Rl = H, R2 = OGlu, R3 = R4 = Me
594 Rl = H, R2 = OH, R3 = R4 = Me
944 Rl = H, R2 = OH, R3 = CH20H, R4 = Me
53. ent-Pimarane-8, 15-Tetrahydrofuran
HO'"
596 Rl = H, R2 = CH20H
597 Rl = CH20H, R2 = H
o
598
FIGURE 1. (contd.)
HOH 2V H
AcO I:
1 ......- - -
o
824
54. Cleistanthane
R, \\\
601 Rl = H, R2 = H, R3 = Me
602 Rl = H, R2 = H, = CHO
R3
603 Rl = H, R2 = H, R3 = CH20Ac
604 Rl = OAng , R2 = H, R3 = Me
605 Rl = H, R2 = OH , R3 = CH20AC
606 Rl = OAng , R2 = H, R3 = CH20AC
CHO
II/ ./"1
II~~
o
607
FIGURE 1. (contd.)
'-': 0
III (
"
OH
OH
608
85. Cle ista nth ane , Iso -
OAe
'" <Jo
'1
609
OAe
'" <Jo
"
610
55. ~-Abietane
611
FIGU RE 1. (con td.)
612 Rl = H, R2 = OH
613 Rl = OAc, R2 = H
R2 R;S
614 Rl = H, R2= R3 = Me
615 Rl == OAc, R2 = R3 = Me
616 R1 = H, R2 = Me, R3 = c02H

1054 Rl = H, R2 = Me, R3 = CH20succ
o
617
FIGURE 1. (contd.)
1100
o
83. Erythroxane
976

58. ent-Kaurane
R, \\\
R3
618 Rl R2 = H, R3 R4 = Me
619 Rl = R2 = H, R3 = Me, R4 = CH20H
620 Rl R2 = H, R3 Me, R4 CH20Ac
621 Rl R2 = H, R3 Me, R4 CH2oMeform
FIGURE 1. (contd.)
622 R1 R2 = H, R) = Me, R4 = CH20-P-OH-H-Cinn

623 R1 = OH, R2 = H, R) = Me, R4 = CH20H
624 R1 = R2 = H, R3 = Me, R4 = CHO
625 R1 = R2 = H, R3 = Me, R4 = C02H
626 R1 = R2 = H, R3 = CH20Ae, R4 = Me
635 R1 = R2 = H, R3 = CHO, R4 = Me
926 R1 = R2 H, R3 = C02H, R4 = Me
939 R1 R2 = H, R3 C02H, R4 = CH20Ang
627 R1 = R2 = H, R3 = C02Gly
Me, R4
628 R1 = OH, R2 = H, R3 = Me, R4 = C02H
629 R1 = OAe, R2 = H, R3 = Me, R4 = C02H

630 R1 = OAng, R2 = H, R3 = Me, R4 = C02H
631 R1 = OTig, R2 = H, R3 = Me, R4 = C02H

632 R1 = OCinn, R2 = H, R3 = Me, R4 = C02H
633 R1 = OSen, R2 = H, R3 = Me, R4 = C02H
634 R1 = Oi-Val, R2 = H, R3 = Me, R4 = C02H
643 R1 = R2 = H, R3 = CH20Ang, R4 = C02H

644 Rl R2 H, R) CH20Sen, R4 c02H
645 R1 = R2 = H, R3 = CH20i-Val, R4 = C02H
1000 R1 = H, R2 = OH, R3 = Me, R4 = C02H
639 Rl = H, R2 = OH, R) = H, R4 = C02Me

640 R1 = R2 = H, R3 = OAe, R4 = C02H
FIGURE 1. (contd.)
R"
R,
641 Rl = R2 = H, R3 = a-OH, R4 = H
642 Rl = R2 = H, R3 = a-OAe, R4 H
796 Rl = R2 = H, R3 = 13-0Ae, R4 H
646 Rl = R2 = R3 = H, R4 = a-OH
647 Rl = R2 = R3 = H, R4 = 13-0H
648 Rl = R2 = R3 = H, R4 = a-OAe
649 Rl = R2 = R3 = H, R4 = a-OAng
650 Rl = R2 = R3 H, R4 = a-OTig
651 Rl R2 R3 = H, R4 = a-OSen
652 Rl = R2 l\3 = H, R4 = a-Oi-Val
653 Rl R2 R3 H, R4 a-02-Mac
654 Rl = R2 = R3 H, R4 = a-Oi-But
655 Rl = R2 = R3 H, R4 = a-OCinn
656 Rl = R2 R3 = H, R4 a-OEpoxyang
657 Rl R2 R3 H, R4 = a-OBenz
818 Rl = R2 = R3 H, R4 = a-02-Mebut-2,3-0H
892 Rl R2 R3 = H, R4 = a-02Mebut
658 Rl R2 = R3 H, R4 = 13-0Ang
659 Rl = R2 = R3 = H, R4 = 13-0Tig
660 Rl = R2 = R3 H, R4 = 13-0Sen
662 Rl = a-OAng, R2 = OH, R3 = R4 = H
FIGURE 1. (con/d.)
663 R1 = a-OCinn, R2 = OH, R3 = R4 = H

664 R1 H, R2 OH, R3 H, R4 = a-OH
665 R1 H, R2 = OH, R3 = H, R4 = a-OAng
666 R1 H, R2 OH, R3 = H, R4 = a-OTig
667 R1 = H, R2 = OH, R3 = H, R4 = a-OAe
668 R1 H, R2 OH, R3 H, R4 = a-OSen
669 R1 H, R2 OH, R3 H, R4 = a-Oi-Va1
670 R1 H, R2 OH, R3 H, R4 = a-OCinn
819 R1 = H, R2 = OH, R3 H, R4 = a-02-Mebut-3-0H
675 R1 ~-OH, R2 OH, R3 = H, R4 = a.-OAng
676 R1 ~-OH, R2 = OH, R3 = H, R4 = a-OSen
677 R1 = ~-OH, R2 OH, R3 H, R4 = a-OTig
OH
OAng
636
661
FIGURE 1. (contd.)
OAng
1007
671 Rl = H, R2 j3-0H, R) = H, R4 = j3-0H

672 Rl = H, R2 = j3-0H, R3 = H, R4 j3-0Ac
637 Rl = H, R2 = j3-0H, R3 = H, R4 = a-OH
869 Rl = OH, R2 = j3-0H, R3 = H, R4 = a-OAng
1260 Rl = H, R2 = j3-0H, R3 = j3-0H, R4 j3-0H
-:/"
673 (Revised to 674)
614
FIGURE 1. (contd.)
R,
997 R1 = H, R2 = R3 = Me (= 720)
721 R1 = OAe, R2 = R3 = Me
722 R1 = H, R2 = Me, R3 CH20Ae
1255 R1 = H, R2 = Me, R3 CHO
723 R1 = H, R2 = Me, R3 C02H
725 R1 = H, R2 = CH20H, R3 = Me
726 R1 H, R2 = R3 = CH20H
728 R1 H, R2 = CH20H, R3 = C02H
724
942
FIGURE 1. (contd.)
690 Rl R2 = R3 = R4 = RS = H
691 Rl OH, R2 = R3 = R4 = RS = H
692 Rl H, R2 = OH, R3 = R4 = RS = H
693 Rl = R2 = H, R3 = OH, R4 = RS = H
694 R1 R2 R3 = H, R4 = OH, RS = H
998 Rl R2 R3 = H, R4 = OEt, RS = H
696 Rl = R2 = R3 = R4 = H, RS = OH
943 Rl = R2 = R3 = R4 = H, RS = OCinn
1256
o
695
FIGURE 1. (contd.)
R,
\\\
697 Rl = R2 = H, R3 = CH2oH, R4 = Me
698 Rl = R2 = H, R3 = R4 = CH20H
699 Rl = R2 = H, R3 = CH2oH, R4 = CH2oP-OH-H-Cinn
946 Rl = R2 = H, R3 = Me, R4 = CHO
700 Rl = R2 = H, R3 = Me, R4 = C02H
701 Rl = R2 = H, R3 = CH20H, R4 = c02H
702 R1 = R2 = H, R3 = CHO, R4 = c02H
703 Rl = R2 = H, R3 = R4 = c02H
707 R1 = Oi-Val, R2 = OH, R3 = Me, R4 = C02H
708 Rl = Oi-But, R2 = OH, R3 = Me, R4 = C02H
R \\\
704 R = Oi-Val
705 R = Oi-But
706 R = OTig
FIGURE 1. (contd.)
\\\
R,
R2 R3
733 Rl H, R2 = R3 = Me
709 Rl = OAng, R2 = R3 = Me
638 Rl = H, R2 = CH20H, R3 = Me
734 Rl H, R2 = Me, R3 = CH20H
710 Rl = H, R2 = Me, R3 = CH20Ang
711 Rl = OAng, R2 = Me, R3 = CHO
735 Rl = H, R2 Me, R3 = CHO
713 Rl = H, R2 = Me, R3 = C02H
712 R = CHO
714 R C02H
715 R = a-OAng
FIGURE 1. (contd.)
716 R = a-OAe
717 R = ~-OAng
718 R = ~-OTig
OH
719
OH
727
1001 Rl = R2 = Me (= 851)
852 Rl = Me, R2 = CH20H
822 Rl = CH20H, R2 = C02H
FIGURE 1. (contd.)
R,
924 Rl = CH2oH, R2 = C02H

925 Rl = R2 = C02H
729 Rl = CHO, R2 = Me
730 Rl = CHO, R2 = CH20H
731 Rl = C02H, R2 Me
732 Rl = c02H, R2 CH20H
736 Rl = COMe, R2 = CH20H
737 Rl = R2 = CHO
738 Rl = CH2oH, R2 = c02H
989 Rl c02H, R2 = CHO
990 Rl = R2 = C02H
740 Rl CHO, R2 = CH2oP-OH-H-Cinn
741 Rl = CH20i-But, R2 C02H
742 Rl = CH20Dodec, R2 = C02H
743 Rl = CH20Tetradec, R2 = C02H
744 Rl = CH20Hexadec, R2 = C02H
FIGURE 1. (contd.)
745 Rl = CH200ctadec, R2 = C02H

812 Rl = c02Me, R2 = C02H
OH
739
OH
746
747 R = ~-OH 815)

748 R = S-OH
FIGURE 1. (contd.)
850
945
R,
678 Rl = R2 = c02H, R3 = OCOCH2CH(CH3)2, R4 = RS = H03so, R6 =H
FIGURE 1. (contd.)
679 Rl = R2 = C02H, R3 = NHCOCH2CH(CH3)2' R4 = CO( CH 2)2C6HS'

RS = OH, R6 = OH
680 Rl = R2 = C02H, R3 = NHCOCH2CH(CH3)2' R4 = CO( CH2)2C6HS'
RS = OL-Rha, R6 = OH
681 Rl = H, R2 = C02H, R3 = OCOCH2CH(CH3)2' R4 = RS = H03S0,
R6 = H
89S Rl = H, R2 = OH
896 Rl = R2 = OH
897
OH
898
FIGURE 1. (contd.)
899
C02 R1
682 Rl = R2 = H, R3 = OH
683 Rl = Glu, R2 = H, R3 = OH
684 Rl = H, R2 = Glu, R3 = OH
685 Rl = R2 = Glu, R3 = OH
686 Rl = Glu, R2 = R3 = H
687 Rl = R2 = Glu, R3 = H
688 Rl ~Glu[21-[11Glu, R2 = Glu, R3 = H
689 Rl ~Glu[21-[11Glu, R2 = H, R3 = OH
FIGURE 1. (contd.)
749
752 R =H
753 R = OH
813
FIGURE 1. (contd.)
R
754 R = CH20H
755 R = CHO
756 R = C02Me
757
HO
758
750 R = H
FIGURE 1. (contd.)
751 R = OH
62. ent-Kaurane, 9,10-seco-
759
866 R = a-OH
867 R = ~-OH
868 R = ~-OAc
o
760 R= H
763 R = OH
FIGURE 1. (contd.)
o
761 R = a-OH
762 R = 13-0H
R,
\\\
764 Rl = OH, R2 = H,= R4 = Me

R3
765 Rl = R2 = H, R3 = Me, R4 = CH20H
766 Rl = R2 = H, R3 = CH20H, R4 = Me
767 Rl = OH, R2 = H, R3 = Me, R4 = CH20H
768 Rl = R2 = OH, R3 = R4 = Me
769 Rl = R2 = H, R3 = Me, R4 = CH20Mal
773 Rl = R2 = H, R3 = Me, R4 = CHO
774 Rl = R2 = H, R3 = Me, R4 = C02H
775 Rl = OH, R2 = H, R3 = Me, R4 = C02H
776 Rl = OTiq, R2 = H, R3 = Me, R4 = C02H
FIGURE 1. (contd.)
770 Rl = OH, R2 = CH20H, R3 = R4 = Me

771 Rl = H, R2 = CH20H, R3 = Me, R4 = CH20H
772 Rl = H, R2 = Me, R3 = R4 = CH20H
817
777 R =H
778 R = OTig
FIGURE 1. (con/d.)
HO
779
III
'" II~(
I /\.'0
780
II/
""'~
781
FIGURE 1. (con/d.)
93. ent-Stachane, 19-Nor-
782
783 Rl = R2 = R3 = H
784 Rl = OH, R2 = R3 = H
785 Rl = H, R2 = OAe, R3 = H
786 Rl = R2 = H, R3 = oAng
787 Rl = R2 = H, R3 = Oi-Val
788 Rl = R2 = H, R3 = Oi-But
814 Rl = R2 = H, R3 = OH
853
FIGURE 1. (contd.)
854
OH
HO \\\
816
789 Rl = OAe, R2 = H
790 Rl = H, R2 = ~-OAe
66. Trachy10bane
H
R3
FIGURE 1. (contd.)
855 R1 = R2 = H, R3 = CHO
791 R1 = R2 = H, R3 = C02H
825 R1 H, R2 = OAe, R3 = c02H
826 R1 = H, R2 OAng, R3 = c02H
827 R1 H, R2 = Oi-Val, R3 c02H
893 R1 = H, R2 = Oi-But, R3 c02H
792 R1 = a-OH, R2 = H, R3 = C02H
1204 R1 = R2 = H, R3 = C02Me
1259 R1 = 13-0H, R2 = H, R3 = C02H
793
794
FIGURE 1. (contd.)
It---o
" H
o !
795
856
67. Helifulvane
FIGURE 1. (contd.)
796 Rl = H, R2 = CH20H
797 Rl = H, = C02H
R2
798 Rl = OH, R2 = C02H
799 Rl = OAe, R2 = C02H
68. Tetraehyrane
o
800
o
847
o
805 Rl = H, R2 = OH
806 Rl = OH, R2 = H
FIGURE 1. (contd.)
78. Villanovane
R4
875 Rl = R2 = H, R3 = CH20H, R4 = CH2oi-val
876 Rl = R2 = H, R3 = CH20Ac, R4 = CH20i-Val
877 Rl = R2 = H, R3 = CH20H, R4 = CH20Meval
878 Rl = R2 = H, R3 = OAc, R4 = CH20MeVal
879 Rl = Oi-Val, R2 = H, R3 = CH20AC, R4 = Me
880 Rl = OMeVal, R2 = H, R3 = CH20AC, R4 = Me
894 Rl = H, R2 = OH, R3 = R4 = Me
69. Lycoctonine
II" I r::: OCH 3
'''\OCH3
\\\
\\
OH
801
FIGURE 1. (contd.)
C
r
11111 OCHJ
II
l CHJ
\\\
\\
OH
802 R =H
803 R = Anth
79. Inulaefane
HO
HO
804
o
o
940 ( 999)
FIGURE 1. (contd.)
CHAPTER 3
Biogenesis
" ... apart from the carbon skeleton of abietic acid with an irregular sequence of 4
isoprene units, the carbon skeletons of all diterpenes are derived from a regular
isoprene tetramer consisting of 4 isoprene units connected head-to-tail... This
structural relationship may be termed the "phytol rule", in analogy to the farnesol
rule of the sesquiterpenes. "
Ruzicka (444, p. 358)
IILI. ent- and Normal-Labdanes

Cyclization of the linear diterpene precursor usually proceeds along two
alternative parallel routes (Figure 2 [po 392]), one leading to the bicyclic
"normal" labdane (normal-labdane) absolute stereochemistry and the other
resulting in its antipodal, enantiomeric (ent-labdane) absolute stereochemistry.
As a consequence of these two parallel biosynthetic routes, diterpenes lack the
homogeneous absolute stereochemistry of the triterpenes.
C-5, C-9, and C-lO substituents are oppositely oriented in the normal- and
ent-Iabdane cyclization products. This distinction between normal- and ent-
labdanes suggests that the linear precursor adopts one of two possible
conformations at the onset of cyclization. The formation of the normal- and
antipodal ent-AB ring junctions and the trans-anti- configuration of these
junctions are governed by the relative orientation of the cyclizing double bonds
within the chairlike conformation of the folded C20 linear precursor (Figure 2).
These alternative cyclizations may be visualized as arising through two different
coilings of the open-chain geranylgeranyl pyrophosphate (GGPP) precursor on
an enzyme surface followed by (1) initiation of cyclization by proton addition to
C-14 of the 14,15-double bond and (2) antiparallel cationic 1,2-additions
resulting from the migration of electrons from the two internal 6,7- and 10,11-
double bonds. Following cyclization to the trans-fused decalin ring system, the
C-4 axial methyl group and H-5 are oriented in the same plane and arranged
trans to one another, a relationship that also exists between the C-lO methyl and
H-9. Likewise, the newly formed C-4-C-5 and C-9-C-1O bonds are in the same
plane and are trans about the C-5-C-1O axis (Figure 2).
386 3. Biogenesis
The hypothetical C-8 carbonium ion resulting from this initial cyclization is
stabilized by several alternative events: (1) proton-loss yielding either the C-7-
C-8 or C-8-C-17 double bond (e.g., Figure 2), (2) neutralization via hydration
or lactone or ether formation and (3) rearrangement. Much of the diterpene
structural variability (Figure 3 [pp. 393-415]) is a consequence of the variety of
rearrangement products resulting from this last mode of stabilization.
In the following discussion, diterpene biogenesis is described in terms of a
hypothetical reaction sequence leading from an appropriate labdane precursor to
a product representative of one of the 103 skeletal types reported from the
Compositae. These skeletal types are arranged in Figure 3 according to their
putative biogenetic relationship.
Regardless of the extensive variability in leaf-resin chemistries found in the
Compositae, all plants of this family presumably biosynthesize gibberellin
diterpenes via a pathway outlined in Figure 4 (p. 416). As gibberellin
biosynthesis (1) appears to be anatomically and functionally distinct from that of
leaf-resin diterpenoids and (2) is regularly reviewed in the literature, it will not
be discussed here.
I1Ll.l. Seco- and Nor-Labdane Skeletons

Ring cleavage and decarboxylation of labdanes have generated several normal-
(Figure 3, Skeleton Nos. 23, 24, 25, 26, 27,87 and 89) and ent- (Figure 3, Nos.
41, 42, 43, 44, 45 and 75) seco- and nor-Iabdane skeletons.
ent-Labdanes of Ayapana amygdalin a and their C-17 nor-homologs (Figure
5 (p. 417); 113) fit well into a biogenetic scheme originating from the proposed
precursor 337. 8,17 -epoxidation and subsequent hydration to produce 343
facilitates loss of C-17 to give compounds with the C-17 -nor labdane skeleton
(i.e. 467 and 468). An alternative route leads to compounds (339-342, 344, 345)
with a C-17 aldehyde or carboxyl function.
Chrysothamnus paniculatus yielded a skeleton resembling the seco-
(cleaved) product of a common grindelane precursor, 172 (Figure 6 (p. 418);
341). This 8,9-seco-grindelane skeleton (Figure 3, No. 25) distinguishes 223, a
compound variously named chrysothame and strictanonic acid. Another skeleton
of seco- origin reported from Nidorella hottentotica displays a ten-membered
ring produced by the cleavage of the C-5-C-1O bond. The proposed relationship
of representatives of this skeleton and structurally related, co-occurring normal-
labdanes is depicted in Figure 7 (p. 419) (155).
III.l.2. Rearranged Labdanes

Rearranged labdane skeletons arise via a series of associated hydride and methyl
shifts, usually involving concerted trans-migrations of the participating substi-
tuents.
1//.1.2.1. Normal-Labdane Series

Among the normal-labdanes, the simplest rearrangement product, the relhaniane
skeleton (Figure 3, No. 28), results from the concerted migration of C-9a-H to
ent- and Normal-Labdanes 387
C-8 and C-IOJ3-methyl to C-9 (Figure 8 Scheme 2 [po 420]). C-l proton loss and
C-I-C-I0 double bond formation complete the biogenesis proposed for the
Re/hania acerosa compound, relhania acid, 231 (Figure 8, Scheme 1 (p. 420);
90). Alternatively, migration of H-5 to C-1O and deprotonation of C-6 are the
final steps of the proposed biogenesis for the Koanophyllon cong/obatum
compounds koanophyllic acids A-D (232-235; Scheme 2, Figure 8). As the
absolute stereochemistry of the koanophyllic acid series is not established, their
normal-Iabdane derivation is unproven and only follows the authors' tentative
assignment (42).
The novel chrysolane skeleton (Figure 3, No. 72) probably results from the
rearrangement of a precursor resembling 6J3-hydroxy-grindelic acid (172). In
this scheme, migration of the C-1O methyl sets in motion a complicated series of
events terminating in the aromatic chrysolane skeleton reported from Chryso-
thamnus panicu/atus (Figure 9 [po 421]; 341).
Examples of the clerodane skeleton, the most common rearrangement
product, can be further subdivided into cis- and trans-fused decalin forms
(Figure 10 [po 422]). In the series of methyl and hydride shifts which make up
the concerted "friedo" or "backbone" rearrangement process culiminating in
the clerodane skeleton, the migrating groups display a trans-diaxial relationship.
For normal-Iabdanes, the expected product of a concerted series of trans-
migrations (C-9a-H to C-8, C-lOJ3-methyl to C-9, C-Sa-H to C-lO, and C-4J3-
methyl to C-S) would be the trans-clerodane (Figure 3, No. 29; Figure 10).
There is as yet no proof that this normal-Iabdane-based pathway operates within
the Compositae. However, the cis-clerodane skeleton (Figure 3, No. 31; Figure
10) which differs from the trans-version in the orientation of the C-S methyl is
well represented. Biogenetically, the existence of the cis-form is explained by a
sequence of concerted trans-migrations (C-9a-H to C-8, C-1OJ3-methyl to C-9
and C-5a-H to C-IO) culminating in the formation of a carbonium ion at C-S.
The AB cis-fused ring system would then result from the migration of the C-4a-
methyl to C-S, followed by deprotonation at C-3.
III.I.2.2. ent-Labdane Series

Steps proposed for the biogenesis of rearranged ent-Iabdanes appear to
correspond to the mechanisms indicated for the normal-Iabdanes, differing only
in the opposite orientivity of the migrating groups.
The simplest rearranged ent-Iabdane is the ent-friedolabdane skeleton (Figure
3, No. 9S). A proposed migration sequence for this structure begins with a
hydride shift from C-9(J3-H) to C-8, followed by a methyl shift from C-1O(a-
methyl) to C-9 and hydride shift from C-5(J3-H) to C-1O and terminates in C-6
deprotonation and C-S-C-6 double bond formation (e.g., 1059).
In contrast to the normal-clerodanes, both cis- and trans-fused ent-clerodanes
are well documented (Figure 3, Nos. SO and 46, respectively). Mechanistically,
the proposed steps of ent-clerodane biogenesis differ from those of the normal-
series only in the opposite orientation of the corresponding migrating hydride or
methyl group (Figure 10).
388 3. Biogenesis
IILl.3. Seco-, Nor- and Rearranged Clerodane Skeletons

The next level of skeletal complexity is expressed by seco-, rearranged and nor-
derivatives of both normal- and ent-clerodanes. Such skeletons (e.g., Figure 3,
No. 41) tend to have relatively narrow distributions, often being reported from a
single source.
Rearrangement of an ent-clerodane precursor results in a series of skeletal
types some of which are shared by two genera, the Astereae member, Conyza
(83), and the Inuleae taxon, Printzia (165). These include the printzianes
(Figure 3, No. 47; Figure 11 [po 423], 571, 572, 915), conyscabranes (Figure 3,
No. 76; Figure 11, 917-920) and 5,1O-seco-clerodanes (Figure 3, No. 48;
Figure 11, 573, 912). Another rearranged ent-clerodane skeleton, solidagonane,
(Figure 3, No. 47; Figure 11 [po 423], 571, 572, 915), conyscabranes (Figure 3,
solidagonal acid (960), which was probably derived from a kolavenic acid (495)-
like precursor (Figure 12 [po 424]).
III.2. Tricyclic Diterpenes

Instead of rearrangement to clerodanes and related bicyclic skeletons, the
hypothetical product of labdane formation, labdadienyl pyrophosphate, can
cyclize to produce either tricyclic pimara-8(9), 15-diene or its 8(14)-isomer. The
simplest mechanism for this process is as follows: attack at C-13 by electrons of
the exocyclic double bond (S~ reaction) is followed by migration of the double
bond from C-13 and elimination of the pyrophosphate group from the allylic
position. The resulting intermediate tricyclic cation at C-8 is stabilized by proton
elimination at C-9 or C-14 (e.g., Figure 13 [po 425] 274). The resulting
skeletons are referred to as sandaracopimaranes or normal-pimaranes (Figure 3,
No. 32) if derived from the normal-Iabdane precursor or ent-pimaranes (Figure
3, No. 52) if formed from an ent-Iabdane.
Tricyclic compounds with the epimeric arrangement of methyl and vinyl
substituents at C-13 often occur as pairs, e.g., rimuene and ent-rimuene (Figure
14A [po 426]), suggesting that electron addition from the exocyclic methylene
can occur at either face of the double bond depending on the stereo selectivity of
the enzyme involved. (The two examples, rimuene and en t-rimuene , also
illustrate that the prefix ent- does not always refer to compounds of ent-Iabdane
origin.) Frequent reports of such C-13 epimeric pairs suggest that enzyme
stereospecificity is low.
Instead of stabilization of the pimarane intermediate by proton elimination at
C-9 or C-14, several further rearrangement processes can occur. For example,
the cassane (Figure 3, No. 34) and abietane (Figure 3, No. 37) skeletons can
result from alternative methyl migrations (Figure 13). The rosane skeleton
(Figure 3, No. 35; Figure 14B [po 426], 881-889) can also be generated by
methyl migration and stabilized by a variety of routes as demonstrated by the
chemistry of Trichogonia (Figure 14B, 183).
The abietane skeleton that Ruzicka excluded from the "phytol rule" (444) can
Biosynthetic Evidence 389
be derived in a straightforward manner from either a normal- or ent-pimarane

precursor (Figures 13 and 15 [po 427], respectively). Representatives of both
normal- and ent-abietanes (Figure 3, Nos. 37 and 55, respectively) have been
reported from the Compositae.
In addition to the ent-abietane skeleton, other tricyclic ent-pimarane derived
ring skeletons have been reported (Figure 15): Cleistanthanes and isocleistan-
thanes were detected in Brickellia eupatoriedes (59) and erythroxanes were
identified in Helichrysum refluxum (450). The absolute configuration (5R,
lOR) of the Brickellia cleistanthanes is identical to that reported for the
cleistanthanes of the Euphorbiaceae, but antipodal to those (5S, lOS) of the
Velloziaceae (Vellozia) (Figure 16 [po 428]; 427).
A critopappus confertus (Eupatorieae) produces a pair of unusual tricarbocy-
clic compounds, 617 and 618, that do no result from the cyclization processes
described above. A biogenetic scheme for these constituents (Figure 17 [po 429])
invokes an aldol condensation reaction to link C-ll and C-17 (184).
III. 3. Tetracyclic Diterpenes

The hypothetical tricyclic pimarenyl cation can either undergo further cycliza-
tion to yield a tetracyclic cation which eliminates a proton to give an ent-
stachane (ent-beyerane; Figure 18, Route I [po 430]) or form alternative
protonated-cyclopropane-containing intermediates (Figure 18, Routes II and
III). Through either simple proton elimination or more complicated processes, a
variety of tetra- and pentacyclic skeletons are produced via these cyclopropanoid
intermediates. With one reported exception, normal-stachane (Figure 3, No.
73), all these polycyclics are members of the ent-series (Figure 18): ent-
stachane, ent-atisirane, ent-kaurane, en t-trachylobane , ent-helifulvane, ent-
tetrachyrane and ent-villanovane (Figure 3, Nos. 64,65,58,66,67,68, and 78,
respectively).
111.4. Biosynthetic Evidence

Assuming that similar enzymes and enzyme systems are involved in the
biosynthesis of both gibberellins and resin diterpenes, the relative wealth of
biosynthetic data concerning the ent-kaurane-derived gibberellins may provide
some insight into resin diterpene biogenesis. Three aspects of gibberellin
biosynthesis seem pertinent to understanding resin diterpene distribution in the
Compositae. The first is the existence of two discrete and separable enzymatic
processes, activities A and B. Activity A cyclizes geranylgeranyl pyrophosphate
(GGPP) to give the labdane intermediate and B completes the cyclization process
to yield ent-kaurene and/or other polycyclic structures. The second is the role of
plastid compartmentation in the segregation of diterpene synthesis from other
terpenoid biosynthetic processes. Further separation of biosynthetic processes is
suggested by evidence that AB cyclization activity is a product of soluble
390 3. Biogenesis
enzymes (313) from which the diterpene is passed to membrane-bound mixed

function oxygenases (497). The third is the role of GGPP as a key branch-point
metabolite in polyisoprenoid metabolism. Each aspect will be discussed in detail
below.
IIl.4.I. Diterpene Biosynthesis: AB Activity

The presence of two separable enzymatic activities associated with polycyclic
diterpene (i.e., ent-kaurene) biosynthesis suggests that inactivation of the first
(A inactivation) could result in the total absence of cyclic diterpenes and
inactivation of the second (B inactivation) would lead to production of only
labdanes and related bicyclic structures. Inactivation of A activity would prevent
the cyclization of GGPP to the bicyclic intermediate. For the bicyclic product of
A activity, absence of B activity would eliminate its role as precursor to ent-
kaurane. If the enzymes of resin diterpene biosynthesis resemble those of
gibberellin biosynthesis, the A and B activities serve as a model regulatory
system accounting for many observed resin chemistry differences between plant
groups. The largely tetracyclic diterpenoid chemistry of the tribe Heliantheae is
radically different from the predominantly labdane and clerodane chemistries of
the Astereae and Eupatorieae. Another large tribe, the Vernonieae yielded no
significant reports of diterpenes despite intensive chemical analysis. Such
widespread patters could be explained by a regulatory system based on either A
or B inactivation.
In castor bean cell-free extracts, enzyme activity could be further differenti-
ated into discrete (1) A activity, (2) AB activity which produced a range of
polycyclic diterpenes including ent-sandaracopimara-8(l4), 16-diene, ent-be-
yerene, ent-trachylobane and ent-kaurene, and (3) discrete B activities that each
correspond to distinct catalytic sites for the production of individual end
products (e.g. sandaracopimara-8(14),16-diene) (497). The activation/inactiva-
tion of different B activities could account for major differences observed in the
resin chemistries of large taxa. For example, a segment of the tribe Calenduleae
is characterized by sandaracopimarane-type diterpenes.
IIl.4.2. Soluble Cyc1ization and Membrane-bound Oxgenation

Enzymes
Kaurene synthetase (a term used collectively for A and B activities) appears to be
a soluble stromal enzyme weakly associated with plastid membranes (437).
Evidence from gibberellin biosynthesis suggests that subsequent to cyclization,
the lipophilic ent-kaurene intermediate proceeds through a series of oxidation
reactions catalyzed by a group of membrane-bound microsomal mixed function
oxidases. Further oxidation ofthe more-polar product is evidently carried out by
soluble oxidase enzymes to yield various gibberellins. The membrane-bound
enzymes belong to the class of oxidases that require reduced pyridine nucleotide
and O2 as co-substrates and are cytochrome P-450 dependent. Members of this
enzyme class may be more generally involved with diterpene oxygenation (497).
Biosynthetic Evidence 391
These results suggest a clear distinction between the biogenetic steps

associated with the cyclization processes (AB activity) and subsequent oxidative
modifications. Although the extent to which gibberellin biosynthesis can be
generalized to other diterpenes is unknown, the organization of its biosynthesis
provides a useful framework for interpreting resin diterpene structural variabil-
ity.
III.4.3. GGPP and Diterpene Distribution

GGPP is a key branch point metabolite of polyisoprenoid metabolism. Apart
from the cyclic diterpenes, it is the precursor of the tetraterpenes (carotenes,
xanthophylls), and acyclic diterpenes (phytol). Cyclic diterpenes compete with
compounds of established importance for either GGPP or its precursors (e.g.,
farnesyl pyrophosphate). The "spotty" nature of resin diterpene distribution
may in part be explained by the obvious demand for carotenoids and phytyls and
the relatively unestablished requirement for these nongibberellin diterpenes.
III.4.4. Compartmentation and Diterpene/Sesquiterpene Expression

GGPP biosynthesis and its conversion to acyclic, macrocyclic, bicyclic and
polycyclic diterpenes may be localized within specific plastid compartments
(498). This proposal fits into a broader scheme in which key isoprenoid metabolic
branch points leading to mono-, sesqui-, and diterpenes are selectively activated
only within certain membrane-bound sites. Compartmentation would then help to
regulate the proximity of chain-length specific prenyl transferases to the
appropriate C lO , C 15 , and C20 cyclases, and modifying enzymes. Strict metabolic
regulation would then be possible within a given compartment (234).
This model can be applied to the terpene-producing trichomes that typify
Compositae species. Trichomes are clearly the primary sites of physical
compartmentation of terpenoid biosynthesis. "Multiple compartmentalized
biosynthetic sites" probably occur within the secretory cells of the trichomes
(234). Thus, expression of a well-developed sesquiterpene and/or diterpene
chemistry in a plant may only be the result of the activation of specific,
preexisting "biosynthetic sites."
This view of compartmentation as an important regulatory factor in terpenoid
biosynthesis (498) may help explain the extraordinary diversity of sesqui- and
diterpene chemistries found even within groups of closely related species. A
survey of glandular terpenoid chemistries reveals that some species are
predominantly sesquiterpene producers, others are diterpene producers, and still
others produce copious amounts of both. Such diversity even within clusters of
related species suggests that the expression of the regulatory process controlling
the activation/inactivation of compartmentalized sesqui- and diterpene biosyn-
thesis may playa role in the speciation process.
392 3. Biogenesis
13 ~/~ ~)O
~15~~(
H+14
1612 4
10 9 ~7'~ ~OPP
17 8
I 1
Normol-Iobdone
12 14
13
opp
2
3
opp 3
19
...................................................................................................................................
opp
(
ent-Lobdone
V opp
FIGURE 2. Alternative cyclizations of geranylgeranyl pyrophosphate to produce normal-

and ent-labdane products.
Figure 3. Linear and Cyclic Diterpene Skeletal Types 393
1. Geranylnerol
2. Geranylgeraniol
3. Gerranyllinalool
4. Phytol-derived
6. Acanthoaustralane-6,11-epoxide
8. Geranylgeraniol-18,8-lactone
9. Oxepane
86. Melcanthane
10. Mikanofurane
11. Centipedane
12. Geranylgeraniol-1,20-1actone
14. Isocembrene
15. Geranylnerol-11,14-a-epoxide
A. Bicyclic (regular)
16. Normal-labdane
17. Grindelane
18. Normal-labdane, 8,13-epoxide-
19. Normal-labdane, 8,12-epoxide-
20. Normal-labdane-15,16-lactone
FIGURE 3. Linear diterpene skeletal types and cyclic diterpene skeletal types derived
from normal and ent-Iabdane precursors.
394 3. Biogenesis
21. Norma1-1abdane-20,12-1actone
22. Normal-1abdane spiroketal
88. Norma1-labdane-15,12-lactone
B. Bicyclic (seco- or nor-)

23. Normal-labdane, 7,8-seco-
24. Normal-labdane, 3,4-seco-
25. Grindelane, 8,9-seco-
89. Grindelane, 19-nor-
26. Grindelane, 8,17-bis-nor-8,9-seco-
27. Normal-labdane-20,12-lactone, 5,10-seco-
87. Hexanorlabdane
100. Normal labdane, 14,15-bisnor-
101. Normal labdane, 13,14,15,16-tetranor-
C. Bicyc1ic (irregular)
28. Relhaniane
29. trans-Norma1-c1erodane
30. C1erodane, 5,10-seco-
31. cis-Normal-clerodane
72. Chrysolane
III. Normal-Tricarbocyclics and Derivatives

32. Sandaracopimarane (Normal-pimarane)
33. Sandaracopimarane-20,8-hemiacetal
34. Cassane
35. Rosane
36. Sandaracopimarane, 19-nor-13-epi-
FIGURE 3. (contd.)
37. Normal-abietane
94. Stevisalane
IV. Normal Tetracarbocyclics

73. Normal-stachane
A. Bicyclic (regular)
3S. ent-Labdane
39. ent-Labdane-19,6-lactone
40. ent-Labdane-S,13-epoxide-15,16-hemiacetal
97. ent-Labdane dimer
9S. ent-Manoyl oxide, 13-epi-
99. ent-Manoyl oxide
B. Bicyclic (seco- or nor-)

4l. ent-Labdane, 17-nor-
42. ent-Labdane, 15-nor-
43. ent-Labdane, 14,15-bis-nor-
44. ent-Labdane, 13,14,15,16-tetra-nor-
45. ent-Labdane, 7,S-seco-
74. ent-Labdane, 18-nor-
C. Bicyclic (irregular)
95. Friedolabdane
47. Printziane
FIGURE 3. (contd.)
396 3. Biogenesis
76. Conyscabrane
48. ~-Cierodane, 5,10-seco-
96. trans-ent-c1erodane, 17-nor-
49. trans-ent-Clerodane, 13,14,15,16-tetra-nor-
82. Solidagonane
102. Friedolabdane, 3,4-seco-ent-
103. Friedo1abdane, Rearranged 2,3-seco-ent-
VI. ent-Tricarbocyclics
51. ent-Labdane, cyclopropyl-
77. Gutierreziane
52. ent-pimarane
53. ~-Pimarane-8,15-tetrahydrofuran

85. Cleistanthane, iso-
55. ~-Abietane
57. Acritoconfertane-acetal
83. Erythroxane

58. ~-kaurane
59. ent-Kaurane, 17-nor-

60. ~-Kaurane, 18-nor-
61. ent-Kaurane, 19-nor-
62. ~-Kaurane, 9,10-seco-
63. ~-Kaurane-19,10-lactone, 9,10-seco-
FIGURE 3. (contd.)
81. ent-Kaurane-19,6-1actone, 9,10-seco-

93. ent-Stachane, 19-nor-
66. Trachylobane
67. Helifulvane
68. Tetrachyrane
78. Villanovane
69. Lycoctonine-diterpene

70. Pimarane, 18-nor-
79. Inulaefane
84. Hebeclinane (9,10-seco-labdane)
FIGURE 3. (contd.)
398 3. Biogenesis
5 I / /'
I
..
:I:
0
5
{-
/
~
$(
0
---4~ \
)
~
1I
r- <
IL ....I
\ IaJ
...I ffiz
--
IaJ
t~ I
....I
0
I ~o
II:
IaJ
~ i~
I
/
i l;j
::a
~
::a ...I
to
()
,;,
" -
GO
- 0
GO
-
----
~
~
I:::
C
~
~
;:l
£
~ (~
~ 1
£
IaJ
\
i5z
Ii: IaJ
zIaJ
I- ~
II:
ag
CD
~
l!1
,;,
< •
400 3. Biogenesis
a a
L
<
<
F \
ri
<
0
'---
....
J(
/ 0
~
:r
~
{
~
Q.
.;.
!
.;,
~.;.
-
I
y--
/ ./
!~
~
\
III
L I
c!.
\
"l
i
....
~
I~
w
I
5
0
-
N
~I;;:
C
IJ
'-'
rri
~
;:J
&
~(
~
0
N
2· GERANYLGERANIOL 16· NORMAL-~DANE 17· GRINDELANE
1((1(/0. ~~O
(B~
OH
(" ""T - 'x -, = '
I \
,- / / ,H
sP
I I
20· NORUAL-LABDANE-15,16-LACTONE t 8· NORUAL-~DANE-8,13-EPOXIDE 89· 19-NOR-GRINDELANE
0 :->
/~'( tAl
o·
0C1
(~O ~""~ 0
~
("1 ~ J l,o ~'1 OH f!.l.
'"
~,,~ ~/ ~,~ ,
/ H
21· NORUAL-~DANE-20,12-LACTONE 19· NORUAL-~DANE-8,12-EPOXIDE 25· 8,9-SECO-GRINDELANE
0
H 0 (,'N
/
0-
~\
-: rf/ rt~ OH
(i~~ _--1
~X~ ,) = "
I
;,£r '1\ H '~y
?\
, \ 0
88· NORMAL-LABDANE-15.12-LACTONE 22· NORMAL-LABDANE SPIROKETAL 28· 8,17-BlS-NOR-8.9-SECO-
GRINDELANE
if °
Ir- \
)' °
/ :><0
OH
cif)=O -'f'i'OIC'
C)(::~~ ° y;:'O
'Tj
~.
;' \ H
(ttl
'x :
/ \ H
~-../
/ \ H ° @
t;>
27· 5.10-SECO-NORt.lAL-
t""
~.
LABDANE-20,12-LACTONE
~
....
~IC\ 8-
<:r/ n
'<
c..
(=l'
8°'. I o
H
'X!~
f'
tZl
~
FIGURE 3, (contd,)
~
Q
'&
'"
~
t;>
404 3. Biogenesis
o
:z:
o
o
29. TRANS-NORMAL-CLERODANE 30· 5,1 O-SECO-ClERODANE
"Ii
~.
31. CIS-NORMAl.-CLERODANE 90· TRICYClOCLERODANE ..,t1>
:->
t""'
~.
0 !!l
~
8.
n
'<
Q..
r;.
0
~.
94· STEVlSAlJ\NE ~:;3

t1>
en
H~ [
~
e:..
0-3
~
t1>
'"
FIGURE
~
3. (contd.)
~
VI
406 3. Biogenesis
I
i
~I
eiI
-..,&:
o
-
Z
I
."
,e
k.I
r-- W
!
~
~ ~
k.I
i
:ff
It:
0
z
,;;
i
~
~
e
III
~
§
~
~
::a
,\ // w
X
I
co
d
N
I
W
I
it
I
it
0
i
~
I~
:!l
408 3. Biogenesis
11.1
11.1
I
11.1
II ~
11.1
I
~
III
:5
I
ffiI 0::
I ~
11.1
I
I§
Z
iI 0::
0
I
,... Z
.
It) I :I:
tID
,......
N ; 11111
w
~
~I
~ !Ew
~I I
It:
w
!Z z0 ~III
~
W
I ~
It: I
0
z I
!Z
1&.1
I
III
co
.- I
0
i5
I
.n
.- fd
I/) .; III
I
.-
~ ri lID
,..: ~
s:::
~ ..;.
.... ~ 8
'-'
rri
~
::>
£
.j>.
o
-
38· ENT-LABOANE 47· PRINTZIANE
HO
o
95· ENT-FRIEDOlABDANE 76· CONYSCABRANE ~
t:I:j
j.
~ tn·
o
46· TRANS-ENT-CLEROOANE 48· 5.10-SECO-ENT-CLERODANE

""zt§
0
0::
""0
..J
I
!z
""Z ""en
I
t
~
~
0
0
IS I
a ..J
0
I
0::
0
Z
~ ~., !z I
""enI
~
""~ ~ I
I
...iii
u:I "ti
.....
!:::
0
~
0:: ... ~
C
...
0
z ..;
::i r-i
I
r-.. ,,;
~ ~
oA ::r
~
..,c:. rD 0,
..,.
;:J
CJI
~"
~
N
38· ENT-LABDANE -
51· CYClOPROPYL-ENT-LABDANE 52· ENT -P'UARANE 83· ERYTHROXANE
:->
t;x;
~.
~f!).
'"
56· ACRITOCONFERTANE 53· ENT-PIUARANE-8. 15-TETRAHYDROFURAN
/
r<:
57- ACRITOCONF'ERTANE-ACETAL 54- CLEISTANTHANE 85- ISOCLEISTANTHANE
1 111, /
, {.O\-H " 11, /
~O
'"T1
~ ~.
w
77 - GUTIERREZIANE 55- ENT-ABIETANE r'
~.
8-
n
'<
(")
~
~
o o
f·
[
FIGURE 3. (contd.)
~
~
'g
'"
oj:>.
w
-
.j::>.
38· ENT-LABDANE 59· 17-NOR-ENT-KAURANE .j::>.
-
64· ENT -STACHANE 58· ENT-KAURANE /' 60· 18-NOR-ENT-KAURANE
w
c:;
i'
f!J.
'"
67· HEUFULVANE 68· TETRACHYRANE

" 61· 19-NOR-ENT-KAURANE
o
78· VlUANOVANE 66· TRACHYLOBANE 62· 9,1 O-SECO-ENT-KAURANE
"ti
~.
@
w
C
~
65· ATISIRANE 69· LYCOCTONINE ~
OCH 3 8-
n
OCH 3 "" r::: '<
"'\OCH3 !2.
"'t:I.
\,\
\\
OH
f"
tI'.l
[
~
FIGURE 3. (contd.) Q
'H
.j:.
VI
-
0\
-""'"
GENERAL ROUTE OF DITERPENOID BIOGENESIS
~
pp
ttl
~.
....
~.
'"
GERANYLGERANYL PYROPHOSPHATE ENT-LABDANE
f-oH
ENT-KAURANE C19-GIBBERELLIN
FIGURE 4. Generalized route of "universal" diterpene biogenesis culminating in Cwgibberellin.

C02 H
"r1
HO '\\\ O<i'
HO ", s::
@
VI
I a Ia
< [H2 0] C02 H
C02 H
l8-
t:C
~.
(1)
~
~.
HO ",
'"o
...,
HO'"
~
343 ";'
339 R,=H,R2 =CHO 341 R,=H,R2 =CHO
340 R, =CHO,R2 =H 342 R,=CHO,R2 =H

~
'"~
344 R,=H,R2 =C02 H '"
8.
345 R,=H,R2 =C02 H (13E) is
'"1
::r
HO'" l
o
(JQ
'"
468 (C-3 KETO)
FIGURE 5. Proposed biogenesis of ent-Iabdanes and nor-homologs reported from Ayapana (Eupatorieae, 113).
~
- .I
-
418 3. Biogenesis
I \
o 189
FIGURE 6. Proposed route of biogenesis of the 8,9-seco-grinde1ane chrysothame (223)

from grinde1ic acid (167) in Chrysothamnus paniculatus (Astereae) (341).
Figure 7, Proposed Route of Biogenesis 419
;'/-:. OH -
OR 225 R=H
214
/ 226 R=Ang
227 R=i-8ut
228 R=2-MeBut
229 R=i-Val
= 230
OAng
FIGURE 7, Proposed route of biogenesis of the 5,1O-seco-normal-labdanes, 225-230,
from a common precursor (similar to 214) occurring in Nidorella hottentotica (155),
420 3. Biogenesis
,. Relhonio oceroso
2· Koonophyllon conglobotum
FIGURE 8. Diterpene skeleton products of the rearrangement of normal-labdane

precursors: alternative routes for the biogenesis of diterpenes with the relhaniane
skeleton, scheme 1 for compounds reported from Relhania acerosa (90) and scheme 2
for compounds from Koanophyl/on conglobatum (42).
Figure 9. Proposed Biogenesis of the Chrysolane Compound 421
o o OH
+ OH
~ -
-:.
~
FIGURE 9. Proposed biogenesis of the chrysolane compound, 271, from the 6/3-hydroxy-
grindelic acid precursor, 172 in Chrysothamnus paniculatus (341).
~
NORMAL
LABDANES: -H+
----+ ---+ ~ ----+
-H+
- ----+
H
~
tl:j
----------------------------------
j.
1';;.
ENT-LABDANES:
+
-H
TRANS-CLERODANE
--
- H+
------+ ----+
H
----
FIGURE 10. Proposed biogenetic routes for the four clerodane (kolavane) sketetal types.
COzHj
....... "-
cj
~ H ~ H ~0
'T1
0Ci·
c
....
(1)
HO~ !!I72
o j 0 '"tI
'"
....
0
'"0
0
(1)
'"p..
tJ:j
o·
O<l
(1)
::s
~
(S.
919 la-H.<4a-OH 917 1a-H.<4a-OH ::0
HOzC o<r ...... 0 g
920 1B-H.48-QH @"
918 lB-H.4B-OH
'"
HOzC R H
912 R-oAc
FIGURE 11. Proposed biogenetic routes for trans-ent-clerodanes and other related rearranged skeletons
reported from Conyza (Astereae, 83) and Printzia (Inuleae, 165). ...,~
~
C02 H C02 H
~
C:l
~.
C02 H o
H ~.
('f '"
OH
o
H
960
H+
FIGURE 12. A proposed biogenetic route for solidagonane (960), a rearranged clerodane reported from Solidago altissima (143).
SAN DARACOPIMARANE
H
~
CH2 -OPP
H '"I1
~.
a @
.....
Vl
, b t t:t!
t
~.
CASSANE ABIETANE (")

!.
~ g
(t
on
316-318
FIGURE 13. Proposed biogenetic routes for sandaracopimaranes (normal-pimaranes) and related skeletons.
N
"""
VI
426 3. Biogenesis
A·
Rimuene ent-Rimuene
B·
FIGURE 14. Proposed route of rosane biogenesis in Trichogonia (Eupatorieae) (183): A.

an example of C-13 epimeric pair of rosane compounds (note that the prefix "ent-"
refers not to an ent-labdane origin, bot to the C-13 orientivity relationship of this
compound pair; B. biogenetic route for sandaracopimarane and rosane constituents of
Trichogonia.
Figure 15. Proposed Biogenetic Routes 427
ENT -PIUARANE
590
CLEISTANTHANE ENT-ABIETANE
614-616
ERYTHROXANE ISOCLEISTANTHANE
FIGURE 15. Proposed biogenetic routes for tricyclic en t-pimarane , ent-abietane,

erythroxane, cleistanthane and isocleistanthane diterpene skeletons derived from ent-
labdane precursors.
t:,
00
OH
~
t:I:l
1:
'"
Yellozia (Yelloziaceae) 602 Brickellia (Compositce)
FIGURE 16. Cleistanthanes from Brickellia (Compositae) and Vellozia (Velloziaceae).
C02 R
~"OH OAe '"I1

OAe ~.
>-L @
::i
I
'"
8-
OJ
C02 H C02 H jO
~o
~C02H
o
'"-,
is''
~"OH
rt OR
~",O t-H 0
~ _0
H @'
1
~
1100
617 R Ae
= \H o
FIGURE 170 Proposed biogenesis of acritoconfertane (617) and acritoconfertane-acetal (1100) constituents of
Acritopappus confertus (184)0
~
IV
10
w
"""
o
H
1/
.,/
OR
1111
~
ENT -KAURANE tI:l
TETRACHYRANE
i'
[!l.
'"
"
o
FIGURE 18. Tetracarbocyclic skeletons of ent-Iabdane origin and their proposed biogenetic relationship (in part 208).
CHAPTER 4
Diterpene Distribution: Compositae
Green plants possess (1) geranylgeraniol, the required precursor for both
carotenoid and gibberellin biosynthesis, (2) the enzymatic machinery to cyclize
geranylgeraniol (or its isomer) to ent-kaurene, and (3) the enzymes for the
oxidation of ent-kaurene and other diterpene substrates (420). Normally, the
steady-state concentration of the products of these pathways falls below the level
of detectability of all but the most sensitive analytical instruments. By
comparison, the compounds that are the focus of this review constitute an
"abnormal" biosynthetic excess detectable in the form of resins. Often, general
plant metabolism is isolated from these biologically active resins by the
comparmentation of resin biosynthesis and storage within glandular trichomes.
The production of copious trichome resin products raises the question of
whether or not these resins are adaptive. Various proposals have been advanced
regarding the defensive role of such compounds and the link between their
structural variability and the coevolutionary process. However, there is little
evidence linking these compound's biological function to the fine detail of their
structural variability. The extent to which the observed chemical variability is an
expression of past selection for specific novel chemical deterrents rather than the
product of near-random activation of alternative terpenoid biosynthetic pathways
is not known. Thus, in looking at the diterpene variability within the
Compositae, care should be exercised in automatically associating a discrete
adaptive function with each novel chemistry.
Whatever the cause of the variability, chemical variation patterns correlate
with taxonomic boundaries and may prove useful as taxonomic characters.
Consequently, chemical differences between taxa may be useful chemical
indicators of phylogenetic relationships. As a corollary, our understanding of the
factors governing terpenoid biogenesis benefits from superimposing a plant
taxonomic framework on the discussion of diterpene distribution and the
underlying biosynthetic diversity.
IV.l. Sub familial Distribution Patterns

The Compo sitae is so well differentiated from other families that any claims
concerning its affinities are difficult to defend. In contrast, its own internal
432 4. Diterpene Distribution: Compositae
boundaries separating tribes and genera are ill defined, due to complex and
overlapping morphological and ecological diversity (233). No taxonomic
problem better exemplifies these poorly demarcated internal boundaries than the
definition of subfamilies. On this subject, Cronquist noted (233) ...
The classical organization of one subfamily for the Lactuceae, and one for everything
else, remains the best such expression of the pattern of diversity within the family.
Perhaps three subfamilies could be recognized, one for the Lactuceae, one for the radiate
[flowering head type with central flowers displaying regular tubular corollas and
marginal flowers in which part of the corolla is prolonged into a strap-shaped ligule]
tribes, and one for the discoid [flowering head type in which all flowers have regular
tubular corollas] tribes plus the Mutisieae ...
Although alternative classifications have been proposed (226), the findings of
the recent study of subfamilial boundaries by Wagenitz (488) were largely
compatible with Cronquist's view. In the Wagenitz phylogenetic proposal, the
Compositae was divided into two subfamilies, the Asteroideae and Cicho-
rioideae. The Asteroideae was further subdivided into two groups (Table 4 [po
438]). A major area of uncertainty for Wagenitz was the placement of the
Anthemideae in one of these two Asteroideae groups. He opted for group 1, but
admitted that with the exception of a pollen anatomical feature, this tribe could
be equally well situated in group 2. The most unusual aspect of his scheme was
the assignment of the Vernonieae and Eupatorieae to different groups (488).
Traditionally these two tribes had been associated by their lack of ray-flowers
and their purple flower color. Wagenitz considered the Cichorioideae to be more
closely related to group 1 than to group 2.
Distributions of three major natural products groups, sesquiterpene lactones
(458), benzofurans/chromenes(benzopyrans) (429) and diterpenes, were super-
imposed on the Wagenitz arrangement of the Compositae (Table 4). While
sesquiterpene lactones appear to be well-distributed across the tribes, both
diterpenes and benzofurans and pyrans are much more heavily concentrated in
Wagenitz's group 2. Their presence in the group 1 taxa has only rarely been
reported. In support of his separation of the Vernonieae and Eupatorieae, the
former tribe, despite intensive chemical investigation, has yielded no reports of
either diterpenes or bezofurans/pyrans, while the latter is a major producer of
both.
A tribe with uncertain affinities based on nonchemical characters, the
Anthemideae, displays a closer chemical link with group 1. Intensive chemical
analysis of this tribe failed to produce reports of either diterpenes of
benzofurans/pyrans. Finally, the chemistry of the Lactuceae (Cichorioideae)
more closely resembles that of the group 1 tribes, a finding which is in
agreement with Wagenitz.
IV.2. Tribal Affinities

Patterns of diterpene variation are relevant as taxonomic characters to
relationships only within the Wagenitz group 2 tribes. Within this group,
Tribal Affinities 433
diterpene patterns distinguish (1) the Heliantheae because of its ent-kaurane-

based polycyclic profile, (2) the Calenduleae based on its sandaracopimarane
chemistry, and (3) the Eupatorieae and Astereae based on their complex
labdane/clerodane bicyclic profile (Table 5 [pp. 439-440]).
IV.2.1. Heliantheae
Natural products variability within the Heliantheae usually parallels the
extensive variability of morphological features. As noted earlier (458), the
sesquiterpene lactones display as much variability within the Heliantheae as
exists within the entire family. When viewed against this background, the
diterpene chemistry of the Heliantheae seems remarkably uniform. Of the
approximately 180 Heliantheae taxa analyzed, only 29 yielded reports of non-
polycyclic diterpenes. These 29 reports included 16 of linear diterpenes, 9 or
normal-Iabdanes, 1 of ent-Iabdanes, 2 of trans-clerodanes, and 2 of ent-
pimaranes (Table 5). The picture that emerges for this tribe is one of a fairly
uniform kaurane-based polycyclic chemistry and a small group of exceptions,
the majority of which contain linear homologs of the geranylgeraniol precursor.
As yet no significant structural novelty is reported for any diterpene group other
than the polycyclics.
III.2.2. Calenduleae
The Calenduleae is the source for most sandaracopimarane (normal-pimarane)
reports (Table 5). Of the 24 investigated taxa, only two produced exclusively
non-sandaracopimarane chemistries; Dimorphoteca aurantiaca and D.
pseudoaurantiaca gave ent-stachanes. A possibly misleading report (78)
included a series of Garuleum sonchifolium structures drawn as ent-
pimaranes, but referred to as sandaracopimaranes. As two of these structures
were described as being previously reported from G. pinnatifidum, it was
concluded that the structures were drawn incorrectly. Bohlmann and Grenz (79)
suggested that this tribe was divisible into two groups, a sandaracopimarane-
producing group (Dimorphotecha, Osteosperum, Garuleum and Chrysanthe-
moides) and a smaller sandaracopimarane-deficient group (Calenula and
Castalis). Investigations of Calendula and Castalis taxa resulted in the
detection of no diterpenes (79). Dimorphotheca yielded sandaracopimaranes,
but as mentioned above two species produced ent-stachanes.
IV.2.3. Euaptorieae and Astereae

The similar diterpene profiles linking the Astereae and Eupatorieae are notable
because of their relevance to the preliminary outcome of a recent phylogenetic
analysis of the Compositae. The preliminary working cladogram (phylogenetic
tree) resulting from this analysis indicated that these two tribes were a major
monophyletic lineage within the family (K. Bremer, pers. commun.). Parallels
in the diterpene chemistries of these tribes adds to the set of characters shared by
them.
434 4. Diterpene Distribution: Cornpositae
IV.3. Infrageneric Distribution Patterns

As yet, no systematic study focusing on generic-level diterpenoid distribution
patterns has been reported for the Compositae. Consequently, little is known
about how diterpenes vary within groups of related species. As a partial remedy
for this deficiency, diterpene interspecific variation is described for representa-
tive genera of the major diterpene-producing tribes: Eupatorieae (Brickellia,
Stevia), Astereae (Baccharis), Inuleae (Helichrysum), and Heliantheae (Heli-
anthus, Montanoa).
Diterpenoid distribution was contrasted to that of other terpenoids for the two
genera, Baccharis and Helianthus. These two taxa were selected for a more
detailed examination, because their chemistries represented the two major types
of diterpene complements: a bicyclic labdane/clerodane type (Baccharis) and a
polycyclic type (Helianthus).
IV.3.1. Brickellia
Most of the approximately ninety Brickellia (Eupatorieae: Alomiinae) species
inhabit the North American deserts, although three species are South American
disjuncts. The diterpene chemistries of the ten investigated taxa (Table 6 [po
441]; Figure 19 [pp. 457-461]) are remarkably uniform. Normal-Iabdanes often
characterized by novel 2a,3a-hydroxylation/esterification occur in all diter-
pene-producing species. In B. eupatoriedes, these 2a,3a-substituted normal-
labdanes co-occurred with cleistanthanes and other ent-pimarane-derived
skeletal types. Production of normal-Iabdanes together with tri- and polycyclic
ent-Iabdane-derived skeletons is an often-repeated theme in the diterpene
chemistries of Compositae taxa.
IV.3.2. Stevia
The 150 to 300 Stevia species (Eupatorieae: Piqueriinae) range from southwest-
ern North America to northern Argentina. Seventy of its approximately ninety
North American species occur in Mexico (464). Chemical investigation of this
genus has been hastened by the discovery of high concentrations of sweet-tasting
ent-kauranoid glycosides in several of the species, one of which, Stevia
rebaudiana, is currently used as a commercial source of sweetening agents in
Japan and Brazil. Despite the common use of these compounds for sweetening
pickled vegetables, sea foods, soft drinks, soy sauce, and so on, questions have
been raised about possible health risks associated with the consumption of the
diterpene aglycone, steviol (368).
Like Brickellia, Stevia species produces mostly mixtures of normal-Iabdanes
and further-cyclized ent-labdane-derived compounds, specifically ent-kauranes.
In several species, only ent-labdanes or their clerodane derivative were reported
(Table 7 [pp. 442-443]; Figures 20 [pp. 462-463] and 21 [pp. 464-466]). Three
of the ent-kaurane-producing species, S. rebaudiana, S. ovata and S.
Infrageneric Distribution Patterns 435
paniculata, produce glycosides in which glycosidic groups of varying complex-

ity are attached at one or more sites, specifically C-13, C-15, or C-19. The
distribution of such diterpene glycosides inside and outside this genus is
probably underestimated due to the lipophilics-specific extraction methods used
in most laboratories.
IV.3.3. Baccharis
Centered in South America, the approximately four hundred perennial herba-
ceous or shrubby Baccharis species extend in their range into North America
(292). Their closest relatives most likely include Archibaccharis and Conyza
(A. Cronquist, pers. commun.). The dominant lipophilic constituents of the leaf
extracts from 54 taxa are diterpenes, triterpenes, sesquiterpenes, flavonoids, and
other phenolics (Table 8 [pp. 443-446]; Figure 22 [pp. 467-468]). Although
ent-clerodanes are the most frequently reported diterpene components, labdanes
and tetracyclic ent-kaurenes and ent-stachanes are common (Figure 22).
No clear variation pattern emerges from the examination of the diterpene
distribution within this genus. Eighteen of the investigated collections failed to
produce any detectable diterpenes, yielding instead various combinations of
sesqui- and triterpenoids and phenolics. No clear-cut mutual exclusivity is
evident in the distribution of diterpenes and these other terpenoid classes.
The significance of individual negative diterpene reports is difficult to
estimate. This difficulty is highlighted by the observation that of the three taxa
that have been examined twice, Baccharis ramoisissima, B. tucumanensis, and
B. alaternoides, two yielded detectable diterpenes in only one of the two
investigations. Given that little is known about (1) factors governing the plant
developmental stage at which diterpene production is initiated and (2) factors
controlling the rate of production, data for these two taxa suggest that species
reports of diterpene absence be treated cautiously.
Looking more closely at the diterpene-producing species, it is apparent that
Baccharis produces relatively more ent-Iabdanes and related skeletons than
were found in Brickellia and Stevia (Table 9, [pp. 447-449], Figures 23 [po
469], 24 [pp. 470-473], and 25 [pp. 474-475]). The most common of these
skeletons is the 5a,1O{3-trans-ent-clerodane. Among the ent-skeletal classes,
there is a rough mutual exclusivity of the trans-clerodanes and the polycyclic
compounds (e.g., ent-kaurenes). Normal-Iabdanes and derivatives occur rarely
within this genus.
IV.3.4. Helichrysum
The large genus Helichrysum (approx. five hundred species; Inuleae: Gnapha-
liinae) extends through Eurasia, Africa, Madagascar, Australia and New
Zealand. As in Baccharis, many investigated Helichrysum species failed to
yield detectable quantities of diterpenes (171). Of the diterpene-producing
species, the majority produced ent-Iabdane-derived compounds of the kaurane,
trachylobane, helifulvane, and atisirane polycyclic types (Table 10 [pp. 449-
451J, Figures 26 [pp. 476-477], 27 [pp. 478-479], and 28 [pp. 480-481]).

Other species produced chemistries combining novel unicyclic geranylter-
pinenes, related acyclic compounds, normal-labdanes, and ent-labdanes. In one
of two separate reports regarding the same species, H. albirosulatum, (171),
ent-labdanes were identified, although in the other (180) normal-labdanes were
found. The report of a macrocyclic diterpene (isocembrene) from H. subfalca-
tum is the only such report from the Compositae.
IV.3.5. Helianthus
The distribution ofthe New World sunflower genus, Helianthus (fifty species;
Heliantheae: Helianthinae) is centered in North America. It is very closely
related to Viguiera, and in fact the generic distinctions between the two genera
break down in several species (316). Many widespread Helianthus taxa are the
products of hybridization. A summary of the diterpene variability within
Helianthus (Table 11 [pp. 452-455], Figure 29 [pp. 482-483]) shows that while
diterpenes have not been reported from all investigated taxa, many plants
produce resins containing both sesquiterpene lactones and diterpenes. Several
species (e.g., H. glaucophyllus and H. microcephalus) produce resins that are
rich in sesquiterpene lactones (249) but lack diterpenes, while others (e.g. H.
occidentalis and H. rigidus) produce abundant diterpenoids and no detectable
sesquiterpene lactones. Chemical proftles of diterpene-producing Viguiera and
Helianthus species display many similarities (Table 11).
IV.3.6. Montanoa
Montanoa (25 species; Heliantheae:Montanoinae) ranges from northern Mex-
ico to Peru, with the greatest species concentration occurring in southern Mexico
and Guatemala. Although few diterpenes are reported from this genus, their
pharmacological value justifies including a discussion of Montanoa diterpenes.
The focus of attention has been the novel oxepane diterpenes (Figure 30 [po
484]) identified as the abortifacient agent in the medicinal tea brewed from M.
tomentosa (419, 382) (See Chapter 5). Oxepanes have been reported from
seven of the nine investigated Montanoa taxa (Table 12 [po 456]; Figure 30).
The only other reported diterpenes are ent-stachanes, kauranes and related
structures. Typically, oxepanes are present in the extract in lower concentrations
than the co-occurring sesquiterpene lactones.
IV.3.7. Interspecific Variation: An Overview

In Baccharis, Helichrysum, and other genera detectable levels of diterpenes
may typify only a fraction of the species. The absence of detectable quantities of
diterpenes, a trait which can characterize an entire tribe (e.g., Vernonieae) or
groups of genera within tribes, seems also to appear within groups of related
species some other members of which produce diterpenes. As noted in
Infrageneric Distribution Patterns 437
Baccharis, some collections of a species may yield diterpenes while others do

not.
This "spotty" and sometimes unpredictable distribution can have many
possible explanations. Any environmental or developmental factor which
disrupts the proper functioning of glandular tissues can affect diterpene
production. Another important consideration is the central role the diterpene
precursor, geranylgeranyl pyrophosphate, plays in terpenoid biogenesis. Its
biosynthesis is dependent on a supply of farnesyl pyrophosphate (the C I5
precursor of both sesqui- and triterpenes) and isopentenyl pyrophosphate (C 5).
The existence of competing demands for the C I5 precursor is suggested by
instances in which sesquiterpenes (e.g., hydrocarbons, alcohols or lactones)
and/or triterpenes characterize extracts lacking diterpenes. Additionally,
geranylgeraniol is the precursor of phytol, a necessary component of chloro-
phyll, and tetraterpenoids (C 40 ), such as carotenoids. Any of the competing
demands for the C20 , C 15 , or C5 precursors could effect diterpene production.
In summary, several distributional trends characterize the diterpene-produc-
ing species of the Compositae genera:
1. Representatives of both the normal- and ent-series occur within genera and
often within the same species.
2. When normal- and ent-series structures co-occur it is usually as a mixture of
normal-Iabdanes and some tri- or polycyclic ent-Iabdane derivatives.
Normal-series structures infrequently exist as tri- or polycyclics; the most
common of such structures, the normal-pimaranes (sandaracopimaranes),
achieve prominence only within the small tribe Calenduleae.
3. Structural novelty (e.g., oxpanes of Montanoa, 2a,3a-dihydroxylation of
Brickellia) can be diagnostic for groups of related species.
4. Despite early statements regarding the rarity of linear diterpenes in plants
(279), linear diterpenes and their hetero- and carbocyclic derivatives are
hardly rare within genera of the Compositae.
TABLE 4. Distribution of sesquiterpene lactones (SQTL), diterpenes (DIT) ,

chromenes (CHR) , and benzofurans (BENZF) in the Compositae tribes
organized according to Wagenitz (488). Sesquiterpene lactone data are from
458. Chromene and benzofuran data are from 429.
Natural Product Classes Read Type

Tribes l SQTL DIT CRR & BENZF DISC RAD5
Asteroideae:
Group 1:
Vernonieae 216 3 _4 _4 +
Liabeae 16 +
Mutisieae 29 1 2 +
cynareae 2 132 1 +
Arctoteae 13 1 +
Anthemideae 412 +
Group 2:
Eupatorieae 184 118 65 +
Astereae 7 96 15 +
Heliantheae 892 192 33 +
Senecioneae 744 10 30 +
Calenduleae 1 23 1 +
Inuleae 114 29 19 +
Cichorioideae:
Lactuceae 30 ligulate
1 Tribes organized according to Wagenitz (~).

2 Cynareae includes Wagenitz's tribes Cardueae and Echinopeae.
3 Number of reports of compounds belonging to this chemical
class in taxa of this tribe.
4 No. of taxa reported to produce compounds of this chemical
class.
5 Flowering heads are either discoid or radiate.
Table 5. Number of Taxa 439
TABLE 5. The Number of taxa (organized by tribes) reported to produce major

diterpene skeletal types.
Diterpene Tribe
Skel. No. VE EU AS IN HE AN SE CA AR CY MU LA LI AR
Linear
1. 12 1 5
2. 8 1 3
Cyclic
I. Normal
16. 29 9 3 9 1
17. 17
18. 3 2 1
19. 2 5
20. 2
21. 1 1
31. 171
32. 2 1 3 2 20
34. 1
35. 2 1
37. 2 1
I I . ~-
38. 18 10 2 1
39. 1
46. 7 16 1 1
50. 5
52. 2 5 2
55. 4 1
58. 30 17 17 115 5 1 1
64. 239 2
66. 24
Representatives of the major diterpene skeletal types

characteristic of the Heliantheae, Calenduleae, Astereae and
Eupatorieae.
TABLE 5. (contd.).
HEUANTHEAE CAlENDULEAE
.nt-Kouron. Sondoracoplmaron.
(normol- plmoron.)
ASTEREAE
EUPATORIEAE
normol-Lobdon. .nt-Lobdon•
normol-CI.rodon. • nt-CI.rodan.
Table 6. Distribution of Diterpenes 441
TABLE 6. Distribution of diterpenes in Brickellia (Eupatorieae) species.
Brickellia Diterpene Cyclic Classes

Linear Normal Ent-
Species A.lUni. Bi. (L) Bi. (C) Tri. Bi. (L) Bi. (C) Tri. Poly.
B. 511
annulosa
B. 101
argyrolepis 102
122
123
B. 106
corymbosa 108
B. diffusa 97
215
216
217
218
B. eupa- 78 601
toriedes 98 602
99 603
103 604
104 605
105 606
126 607
127 608
128 609
610
B. 126
paniculata
B. 106
squarrosa 107
108
109
B. 991
vernicosa 992
993
994
995
B. veroni- 124
caefolia 125
129
220
B. veroni- 129
caefolia
A. Gray
var. typica
TABLE 7. Distribution of diterpenes in Stevia species.
Stevia Diterpene Cyclic Classes

Linear Normal Ent-
S. berlan- 145
diera 1021
1022
1023
S. bupthal- 649
miflora 650
651
652
S. 641
eupatoria 998
S. 118
jaliscensis
S. lemmonia 1020
S. lucida 415
Lag. var.
Bipontini
S. monar- 143 625
daefolia 153 649
S. 3 421 493 625
myriadenia 23 494 650
651
774
S. origa- 428
noides 429
808
809
810
811
S. ovata 895
896
897
898
899
S. 895
paniculata 896
897
898
899
S. poly- 570
cephala
S. 195 428 682
rebaudiana 429 683
684
685
Table 8. Major Natural Products 443
TABLE 7. (contd.).
Stevia Diterpene Cyclic Classes

Linear Normal Ent-
686
687
688
689
S. sali- 121 154[abs. ster. unknown]
cifolia 1024 429
1025
1026
S. 625
setifera
TABLE 8. Major natural products reported from Baccharis (Astereae).
Terpenoid
Species C20 C30 Cl5 Flavonoid Phenolic Acetylenic
B. alaternoides 6 11 14 16
H.B.K. (1)
Peru
B. alaternoides 16
H.B.K. (2 )
Peru
B. articulata 5,6
(Lam. )Pers.
Arg.
B. caespitosa
(Ruiz and Pavon)
Pers.
Ecua. , Peru, BoL
B. calvescens DC. 6 10,13 14
Braz.
B. cassinaefolia 4 11,12,13 14 20
DC.
Braz.
B. chilco 4,6 10
H.B.K. (1)
CoL
B. chilco 13 14
H.B.K. (2 )
Col. , Peru
B. concinna 8 12,13 14 16
Barroso
TABLE 8. (contd.).
Terpenoid
Species C20 C30 CIS Flavonoid Phenolic Acetylenic
B. conferta 6
H.B.K.
Mex.
B. eggersii 3 11 14
Hieron.
Peru
B. genistelloides 1,6 14
(Lam. )Pers.
Col. , Ecua. , Peru
B. grandicapitu- 6 11 14
lata Hieron.
Peru
B. halimifolia 11
B. helichryi- 19
soides DC.
Braz.
B. heterophylla 10
H.B.K.
B. hutchisonii 6 11 14
Cuatr.
Peru
B. intermixta 2,8 14
Gardn.
Braz.
B. juncea 18
(Lehrn. ) Desf •
Braz.
B. kingii 6 14 17
Cuatr.
Peru
B. latifolia 11,13 14,15
(Ruiz & Pavon)
Pers.
Bolo , Ecua.
B. leptocephala 11 14 16
DC.
Braz.
B. microcephala 6 14
(Less. )DC.
Para.
B. minutiflora 8 12 14
llraz.
Table 8. Major Natural Products 445
TABLE 8. (contd.).
Terpenoid
Species C20 C30 CI5 Flavonoid Phenolic Acetylenic
B. nit ida (Ruiz 4 10 14
& Pav6n)Pers.
Peru
B. oxydonta DC. 2 13 14 16
Braz.
B. peduncu1ata 11 14 20
(Miller)Cabrera
Ven. , Peru
B. polyphylla 8 14
Gardn.
Braz.
B. pylicoides 8 10 14
H.B.K.
B. quitensis 8 12 14
H.B.K.
B. ramoisissima 12 14 16
Gardn. (1)
Braz.
B. ramoisissima 8 18
Gardn. (2 )
Braz.
B. reticularia 11,12,13 14 16
DC.
Braz.
B. salicifolia 6 10,11 17
(Ruiz & Pavon)
Pers.
Col. , Arg. , Chile
B. salzmannii 8 12 14
DC.
Braz.
B. sarothroides 6
A. Gray
B. scandens 14
R. & P.
Peru
B. scoparia 3,5 10,11 14
(L. )Sw.
Jamaica
B. serrulata 13 14 16
(Lam. )Pers.
Braz.
TABLE 8. (contd.).
Terpenoid
Species C20 C30 CIS Flavonoid Phenolic Acetyienic
B. sternbergiana 1,2 14 16 18
Steud.
Peru
B. subdentata 4 10 14
DC.
Braz.
B. tola 2,9 10
Chile
B. tricuneata 6 10
var. lineata
Cuatr.
B. tricuneata 21
var. ruiziana
Cuatr.
Col, Yen.
B.tricuneata 4,5,7 17 19
(L.f)Pers.
var.tricuneata
Col., Yen.
B. trimera 6 17
Braz.
B. trinervis 12,13 14 20
(Lam. )l?ers.
Braz., Mex.
B. trinervis 17 20
var. rhexoides
(H.B.K)Baker
Bo1. , Ecua.
B. truncata 8 12 14 16
B. tucumanensis 6
H. & A. (1 )
Arg.
B. tucumanensis 2 or 3 17
H. & A. (2 )
Arg.
B. ulcina H. & A. 14
Bol. , Ecua.
B. vaccinoides 6 10
H.B.K.
B. varians 16
Gardn.
Braz.
TABLE 9. Distribution of diterpenes reported from Baccharis (Astereae).
Baccharis Diterpene Cyclic Classes

Linear Nonnal Ent-
B. alater- 484
noides 569
B. 510
articulata 527
B. 518
calvescens
B. cassi- 531
naefolia 532
533
B. chilco 529
B. 646
concinna (concinnia) 649
625
B. conferta 521
B. eggersii 965
966
B. geni- 561
stelloides
B. grandi- 963
capitulata
B. 507
hutchisonii 967
B. 363 625
intermixta 364 646
B. kingii 846
B. micro- 561
cephala
B. 618
minutiflora 619
621
624
625
697
698
713
720
TABLE 9. (contd.).

Linear Normal Ent-
Species A./Uni. Bi. (L) Bi. (C) TrL Bi. (L) Bi. (C) Tri. Poly.
729
730
731
732
733
734
735
736
737
738
739
B. nit ida 968
B. 442
oxydonta 443
444
445
446
B. 569 625
polyphylla 646
649
661
B. quitensis 699
740
B. 624
ramosissima 625
B. 518[1033]
salicifolia 904
1070
1093
B. 625
salzmannii 650
B. 518[1033]
sarothroides 1034
B. scoparia 964 969
970
1061
B. stern- 331
bergiana 332
333
334
357
359
TABLE 9. (contd.).

Linear Normal Ent-
B. 529
subdentata
B. tela 455 765
766
771
772
779
780
782
B. 509
tricuneata 527
(L. f. )Pers. 528
var. 529
tricuneata 530
B. 508
tricuneata 518
var. 520
lineata
B. trimera 559
562
563
B. truncata 565 624
(tricuneata?) 625
648
650
B. 110 962
tucumanensis
B.
vaccineides 518[1033J
TABLE 10. Distribution of diterpenes reported from Helichrysum (Inuleae).
Helichrysum Diterpene Cyclic Classes

Linear Normal Ent-
H. acutatum 69
70
71
72
1101
TABLE 10. (contd.).

Linear Normal Ent-
H. 1105 447
albirosulatum 1106 448
1107 449
H. 625
argentissimum
H. aureum 625
(Houtt. ) 629
Merile var. 640
monocephalum 690
H. bellum 625
H. 65
calliconum 66
67
H. chiono- 614 625

sphaerum 783
796
797
H. 132
confertum 137
996
1102
1103
1104
H. cooperi 625
629
640
H. 619
dendroideum 623
626
698
764
765
767
770
77l
H. 728
diosmifolium
H. fulvum 625
774
791
798
799
TABLE 10. (contd.).

Linear Normal Ent-
Species A.!Uni. Bi. (L) Bi. (C) Tri. Bi. (L) Bi. (C) Tri. Poly.
H. 619
heterolasiurn 624
629
640
648
H. 32
Krebsianurn 70
H. 624
miconiifoliurn 625
H. mundii 23
H. 68
nudifoliurn
H. 68
odoratissimurn
H. pallidurn 624
625
640
720
722
H. 447
pi nifo li urn
H. 690
platypterurn
H. refluxurn 976 625

774
791
H. ruderale 640
690
H. 23
subfacultaturn
H. 73
subfalcaturn
H. 430
suterlandii
H. vernurn 447 625
TABLE 11. Major di- and sesquiterpenoids of Helianthus (Heliantheae).
Terpenoids
C20 C15
Species LA PI ST TE IS TR AT VI GE HE FU
HELIANTHUS
l.HELIAN-
THUS
H. annuus 15,18 2 35 38-40 42,43 47 49
19,21-23
28,29
H. ano-
malus
H. argo- 18,33 39 47
phyllus
H. bo1an-
deri
H. debi1is 23,28,29 35-37
subsp. cucu-
merifolius
H. debi1is 23,28,29 34 38
subsp.
debilis
H. deserti-
cola
H. neg1ectus
H. niveus 23,28 39 47
subsp.
canescens
H. niveus 47 48
subsp.
niveus
H. para-
doxus
H. agrestis
H. arizo- 33 39
nensis
H. ci1i- 18,21,33 39 49
aris
H. 1aci- 18,21, 16, 39 42
niatus 23,33 17
H. cusic- 28 39
kii
Table II. Major di- and Sesquiterpenoids 453
TABLE 11. (contd.).
Terpenoids
C20 CIS
Species KAI LA PI ST TE IS TR AT VI GE HE FU
H. graci- 47 48 49
lentus
H. pumilus 47
H. cali- 39 47
fornicus
H. deca- 23,26 1-3 38 45 47
petalus
H. divar- 47
icatus
H. egger-
tii
H. gigan- 23,24,26 5 38 47
teus 28,29
H. grosse- 24,28 35 39 47 49
serratus
H. hir- 23,26 11, 38 47 49
sutus 12
H. maxi- 24 3, 47 49
miliani 5 (50 )
H. mollis 47
H. nut- 23,28 35 39 49
tallii
H. resi- 47
nosus
H. salici- 18,33 39 47
folius
H. schwei- 49
nitzii
H. stru- 7,8 49
mosus
H. tuber- 23,24 3,5 48
osus 26,29
H. glauco- (50 )
phyllus
H. laevigatus
H. micro- (5.0)
cephalus
TABLE 11. (contd.).
Terpenoids
C20 C15
Species KAI LA PI ST TE IS TR AT VI GE HE FU
H. porteri
H. smithii
H. atro-
rubens
H. occi- 21,23,28, 3,5 35- 38, 44
dentalis 29-31 37 39
H. rigi- 23,26,33 38,
dus 39
H. silphi-
oides
H. angus- 23,24, 3,5 49
tifolius 28,33
H. car no- 48
sus
H. flori-
danus
H. hetero- 23,24 48 49
phyllus 25,27 (50)
H. longi-
folius
H. radula 19-21, 35, 41
23,26,29, 36
31-33
H. simu- 23,26,28, 35, 48
1ans 29,31 36
v. bisho- 18,23,24 4,6 15 38

pii
v. cordi- 23
folia
v. dentata 23,24, 6 38
28,29
v. exce1sa 23-25, 49
27,31
V. gramma- 23 13-
tog1ossa 15
V. insig- 23,24 15 43
nis
Table 11. Major di- and Sesquiterpenoids 455
TABLE 11. (contd.).
Terpenoids
C20 CIS
Species KAl LA PI ST TE IS TR AT VI GE HE FU
V. lanceo- 38
lata
V. line- 48 49
aris
V. macu- 23,28,34
lata
V. oaxa- 23
cana
V. pazen- 29 38 46
sis
V. porteri 23,28,29 35
V. procum- 23,24 38
bens
V. quin- 29
queradiata
V. steno- 23,29 34 48
loba
1 KA = Kaurane
LA = ent-Labdane
PI = ent-Pimarane
ST = ent-Stachane
TE = Tetrachyrane
IS Isokaurane
TR Trachylobane
AT = Atisirane
VI = Villanovane
GE ::!:' Germacrolide
HE = Heliangolide
FU = Furanoheliangolide
2 See Figure 19 for representative structures
TABLE 12. Distribution of diterpenes reported from Montanoa (Heliantheae).
Montanoa Diterpene Cyclic Classes

Linear Normal Ent-
Species A./Uni. Bi. (L) Bi. (C) Tri. Bi. (L) Bi. (C) Tri. Poly.
M. atri- 625
plicifolia
M.
frutescens 56[homo1ogj
M. 55
1eucantha
subsp.
arborescens
M. 55
1eucantha
subsp.
1eucantha
M. 55
mollissima
M. 618
pteropoda 619
624
625
649
652
655
690
694
773
M. 55
tomentosa
subsp.
microcephala
M. 55
tomentosa 57
subsp. 1094
tomentosa 1095
1096
1097
1098
1099
M. 56 800
tomentosa
subsp.
xanthiifolia
Figure 19. Structures of Normal-Labdanes 457
SCHEME A
OR ~
HO",
H
RO 101 R = Ang
102 R = TIg 119 X = c-OH,H

CH 20R
129 X = 0
SCHEME B
~
'II
HO'" "
122 R = Ang
RO --? -
123 R = Tig / o =
OH
991 R = C0 2H
220
992 R = C0 2 Me
993 R = CH 2 0H
CH 2 0H 994 R = CH 2 02-Mebut
HO ", ,
~H
995
FIGURE 19. Structures of normal-labdanes reported from Brickellia (Eupatorieae):
compounds with common substitutional patterns (Scheme A) and with unusual 2a,3a-
dihydroxy-pattern (Scheme B). Structures of Brickellia ent-c1erodanes [511], c1eistan-
thanes, etc. [601-609] (Scheme C).
.j:>.
VI
00
SCHEUE B
FROU SCHEUE A
.j:>.
COzH
ri CH2 0R
~
o.
.g
ii€
R,O",
9-
'"
R2 C1" ~
108 R, - H, ~ - Ang
~.
98 R,
109 R, - Ang, R2 - H 97 R, - CHO. . . - .. - .... [ AA, n
o
R2 2-Uebut-2-0H
103 R, - Ue, ~ - H, R;, - Ang
104 R, - Ue, R2 - H, R;, - trana-Clnn

l R3 trana-Clnn
~
'"~.
105 R, - Ue, R2 - H, R3 - cla-Clnn 99 R, Ang
107 R, - Ue, R2 - Ang, R;, - H ~ [ 2-".b.1-2-0H
106 R, - Ue, ~ - H, Ra - Ang
R;, cla-Clnn
CC>,H
H
R,O /"
R20 ",
0 'Tj
124 R, - ~ - H o C~OR ~.
125 R, - H. ~ - 2-Uebut-2-0H @
OH .....
\0
126 R, - H. ~ - Ang
en
R,O '"~
C-13 Orlentlvlty Undefined: 2
127 R, - H. R2 - trana-Clnn R2 0 ",
8@
R2 0 ", '"0
128 R, - H. R2 - cla-Clnn ....,
Z
0
o
.,-/ ~
r
~
0-
r»
~
'"
R;,
R2 0'"
215 Rl - ~ - Ang. R;, - H 218 R, - H. R2 - Ang
216 Rl - ~ - Ang. R;, - a-OH

.j::..
FIGURE 19. (contd.). VI
217 Rl - ~ - Ang. R;, - 8-0H \0
::J:
o ,....,
-£
o
o
......
0::
o
I [0]
R, R CHO
R3
"11/'-/\
"'-6_
R2 \"
'\ 'Tl
d'Q'
607 ..,s::
(lj
601 R, -Me,R2 .. R,,-H ~ .....
:0
602 R, .. CHO, R2 - R3 .. H r/l
603 R, - CH20Ac, R2 - R" .. H

2
8@
604 R, - Me, R2 - OAng, R3 - H OAe '"0
605 R, - CH20Ac, R2 .. H, R3 .. OH Z
0
-
3~
606 R, - CH2 0Ae, ~ - OAng, R3 .. H
~
0..
§
(lj
610 3,4-epoxy '"

FIGURE 19. (contd.).
.(:>.
0-
.....
:I:
N
0
(.J
..,.
C'I
0
0:::
0
N
:I:
(.J
:I:
0 /
//
II..
-:.-:.
~ It')
0)
-··r------.
"r1
~.
@
~
en
~
= OR 2
2
.o:.~ H 8
R, @
143 R, - DAng, R2 - H
'"
o
....,
1021 R - H
Z
o
1023 R - OH 145 R, - H, R2 - Ac
[
1022 R, - OH, R2 - Ac ~
8:
OH OH ~
~ 8-
~
HO
-,-" o~' I
t:1
~.
C-8+ W"" ~
= 1026 ~
'"
FIGURE 20. Structures of normal-Iabdane and related diterpenes reported from Stevia
(Euaptorieae) . .j:>.
0\
w
SCHEUE A C02 H
"'"
~
R,
1 1 H +/ r TH+r
f'-
\ 493 R, - H• R2 - Ue
4 o
~ ~c:? 494 R, ... OAe. R2 ... Ue
0 .......... =
- .......... .,- / 570 R, ... H. R2 - CH20H f"S?
OR, C02H
I-n
------ SCHEUE B
428 R, - R2 - H 415 625 R ... H
429 R, ... Ae. R2 - H 649 R ... OAng
i
~.
808 R1 - Ang, R2 - Ae
650 R - OTig
809 R, - Ang, R2 - H, 12E
651 R - OSen
810 R, - Ac,
~ - H, 12E
811 R, - Ang,
R2 .. Ac, 12E
RI
~ ~
'T1
~.
(il
tv
C02H -
en
641 RI - H, R2 - OH
895 RI ... R2 - H i
(il
998 RI = OEt, R2 - H, 9,1 1db en
896 RI ... OH, R2 ... H S?,
~
~ » / 899 RI coo H, R2 ... Glu
ig
OH
8-
;t ~
OH ~
421 ~
C0 2Glu 0.:
o
897 898
FIGURE 21. Structures of ent-Iabdane and ent-kauranoid diterpenes isolated from Stevia (Eupatorieae): ent-Iabdanes and kaurene mono- and
di-glycosides (Scheme A); C-13-kaurene-glycosides (Scheme B).
f·
en
.j::>.
3:
SCHEME B
SCHEME A
H~
R'~
HO 682 R, = R2
683 R, = Glu.
co
R2
H. R3 = OH
= H. R3 = OH
OR2
0
684 R, = H. R2 = Glu. R3 = OH
HO '2 0
685 R, = R2 = Glu. R3 = OH
20 "
686 R, = Glu. R2 = R3 = H
2
687 R, = R2 = Glu. RJ =H
3 688 R, = B-Glu[2]-[1]Glu. R2 =Glu. R3 = H
689 R, = 8-Glu[2]-[1 ]Glu. R2 = H. R3 = OH

'8 C02R,

Figure 22. Representative Structures 467
DfTERPENES:
UNEAR
1· Phytol (59)
LABDANE
J. normal-Labdan. 2· ent-Labdan. (442-445.«c·)
(202.984.etc.)
CLERODANES
(TRANS-ENT - )
IIIIt
4. (529-533)
8· (484.508-510 • •) 7· (528)
HO
8· .nt-Kauran. 9· ent-Stachan.
(819.824.648-651 .•tc· ) (765.786.771.772.779)
FIGURE 22. Representative structures of di-, and tri-, and sesquiterpenes, flavonoids,
acetophenones, coumarins, and poly acetylenes reported from Baccharis (Astereae). The
numbers assigned to the structures correspond to the numbers listed in Table 8.
TRITERPENES:
10· Oleanalie Acid-type 11.
HO
12· Lupeal-type '3· Squalene
SESQUlTERPENES:
HO",
14· Germaerene-D-iype , 5· Eudeemane-type
F'LAVONOIDS:
OH
, 6· Flavonone-type '7· Flavone-type

Figure 23. Structures of Normal-Labdanes 469
ACETOPHENONE:
·::CO""'f
HO
18·
CHO
COUUARINS: P-COUUARIC ACIDS
CH3~ ~
HO~O~O HoD CHO
19· 21·
POLYACETYlENES:
"z/ ~.
CO,CH3
964 965 R .. CH 20H
966 R - CHO
FIGURE 23. Structures of normal-labdanes reported from Baccharis (Astereae).

SCHEUE A
C~OR
OR
:: ~
C~OR
~ SCHEUEB
OH
::~
CHO
x x
JJ2 X - o-OH. H
442 X-H. H JJl X - o-OH. H
J34 X - 0
443 X - B-OH. H 333 X - 0
444 X - o-OH. H
445 X - B-OSuee OH
446 X - 0
x
I
I
II
I 357 X - o-OH. H
I
I
359 X - 0
455 L
363 Rl - H. R2 - Ac
364 Rl - OAe. R2 - Ac
FIGURE 24. Structures of ent-Iabdanes (Scheme A) and related ent-c1erodanes (Schemes

B, C, and D) reported from Baccharis (Astereae).
Figure 24. Structures of ent-Labdanes and ent-Clerodanes 471
SCHE..,E B
OH
967 R - CHO 0"'01
484
SCHE..,E C
846 R, - R2 - R3 - H
508 R, - "'01, R2 - R3 - H
509 R, - ~ - H, R3 - OH
510 R, - "'01, R2 - OAe, R3 - H
/
518 [1033] R - H
1034 R - OH
1070 R - H, 1,2db
SCHE..,E 0
1093
520 R - H
521 R m OH

MaIO
I 562 R - OH
o
Figure 24. Structures of ent-Labdanes and ent-Clerodanes 473
SCHEWE D
~
o
C-17 OXIOATIO/ ~20 OXIDATION
OH
~/"
R,
o
529R,-R:a-H
OH 530 R, - OAng, Rt - H
966 R, - H, R:a - OAng
~
H\
531 R, - An9, R2 - Sen
\ 0 532 R, - Sen, R:a - Ang
rl969 6,17db 533 R, - Ang, R2 - 2-Webut

o
970
FIGURE 24. (contd,).

474 4. Diterpene Distribution: Compo sitae
720 R, - R, - .... R" - OH

711S R, - .... R, - CHwOH. R" - ... 7211 R, - .... R, - H. R" - CHO
788 R, - CHwOH. Rt - R~ - ... 730 R, - CHwOH. R, - H. R" - CHO
n1 R, - .... R, - R" - CHwOH 731 R, - .... R, - H. R" - C~H
732 R, - CHIOH. R, - H. R" - C~H

n2 R, - R, - CHIOH. R" - ...
182 R, - .... RI - OH. R" - ... 738 R, - CHIOH. R, - H. R" - co ...
737 R, - CHO. R, - H. R" - CHO
73e R, - C~H. R, - H. R~ - CHwOH
7711 R, - CHwOH. R, - ...

7110 R, - .... RJ - CHwOH
FIGURE 25. Structures of ent-stachane and ent-kauranoid diterpenes isolated from Baccharis
(Astereae).
Figure 25. Structures of ent-Stachane and ent-Kauranoid Diterpenes 475
8111 R, - lie, Rt - H
819 R, - CH,OH, Rt - H
821 R, - CH,OCH,OCHO, Rt - H
822 R, - CH,0-p-OH-H-Clnn, Rt - H
~~
824 R, - CHO, Rt - H
82:! R, - CO:IH, Rt - H
848 R, - COwH, Rt - OH
);J~/
848 R, - COwH, Rt - 0Ac
R
849 R, - CO:IH, Rt - ClAng
733 R - ...
e:s0 R, - COwH, Rt - OTlg
134 R - CH,OH
e:sl R, - COwH, Rt - 0Sen
735 R - CHO
eel R, - COzlle, Rt - OH
713 R - COwH
= fyCHO
itrV' I
~
I
/
"""" O-p-OH-H-Clnn
740
687 R - H
898 R - OH
699 R - O-p-OH-H-Clnn
:I<
:z: 0
I I ::z:
0
0
>< >< £ :z:
u
r. r. u
I I I I
Il:: Il::
.., ..,
Il::
N
Il::
N
It)
10
co
10
.....
10
><
C,J
o
\\'--_ _ _ _ _ _ _
:z: _ _ __
4
./
3
2
~
68 'T1
~.
704.5db (il
tv
0\
, OH en
2'
(")
8
(il
'"o
....,
71 4.5db o
~.
69 .a
~
'"
1101 C3a-O-aC6
72 C3B-O-BC6
FIGURE 26. Structures of linear (23, 32), unicyc1ic (65-72, 1101), and macrocyc1ic ~
(isocembrene, 73) diterpenes reported from Helichrysum (lnuleae). -.J
-.J
Il::
oN
::r:
o
::r:
n
Il::
ttl
N
Il::
o
/
•
H CH2 0H
~
x ~
N
-.J
1105 X .. H,H 1102

1103
1106 X = 8-0H,H r
~
~ 1107 X .. 0 sa,
Z
o
[
j
S?
R, R2 ft
132 R, - R2 .. Ue
1
'"
137 R, - C~H, ~ - Me
1104 R, .. Ue, R2 - C02 H

~
FIGURE 27. Structures of normal-Iabdane diterpenes isolated from He/ichrysum (Inuleae). ::cl
480 4, Diterpene Distribution: Compositae
SCHELIE A
430 447 R - H, R - H,H
4~ R - H, X - H,OH
614 SCHELIE 8
976
764 R, - OH, R, - R, - LIe

797 R, - H. R, - CO,H
765 R, - H, R, - CH,OH, R, - LIe
798 R, - OH, R, - CO,H
767 R, - OH, R, - CH,OH, R, - LIe
799 R, - OAe, R, - C0 2H
771 R, ~ H, R, - R, - CH,OH
774 R, - H, R, - CO,H, R, - LIe
FIGURE 28, Structures of ent-labdane (430, 447-449), ent-pimarane (976), ent-abietane

(614), ent-helifulvane (796-799), ent-trachylobane (791), ent-atisirane (783), ent-
stachane (764, 765, 767, 770, 771, 774) (Scheme A), and ent-kauranoid (Scheme B)
diterpenes reported from Helichrysum (Inuleae),
Figure 28. Structures of ent-Labdane and Other Diterpenes 481
SCHEME B
698
720 R - t.le 619 R, - H. R2 - CH 20H

722 R ~ CH 2 0Ac ,I 623 R, - a-OH, R2 - CH 20H
/
/ 624 R, - H, R2 ~ CHO
I 625 R, - H, R2 - C0 2H
OH
ENT-LABDANES
OH
1· R - CH3 4·R-CH3 6·
2· R - CHO 5· R - C~H
3· R - C~H
OR
OAe
C~H
7· 7(8) d·b· 11·

12·
8· 8(9) d·b·
9· 9(11) d·b·
10·
ENT -STACHANES
OH
R
13· R - CH20H 16· R - H
14·R-CHO 17· R ... OH
15· R - C02 H
FIGURE 29. Major diterpenes isolated from Helianthus (Heliantheae). The numbers
assigned to the compounds correspond to the numbers listed in Table 11.
Figure 29, Major Diterpenes 483
ENT -KAURANES
R
18· R, - a-OH, R, - CH,

23· R - H 28· R, - H, R, - OH
19· R, - a-OH, R, - CH,OH 24· 9( 11 )d·b·, R - H 29· R, - H, R, - OAng,OTig, etc'
20· R, - a-OH, R, - Co.,H 25· 9(11 )d·b·, R - 8-0H 30· R, - R, - OH
21· R, - 8-0H, R, - CH, 26· 9(11 )d·b·, R - a-OH
22· R, - 8-0H, R, - CO,H 27· 9(11 )d'b', R - -0
31· 32· 33·
TETRACHYRANE
35· R - CH,OH
38· R, - R. - R, - H
36· R - CHO
39· R, - OH, R. - R, - H
34·
37· R - Co.,H 40· R, - H, R. - OH, R, - H
41· R, - R. - H, R, - -0
("r y
R,
(,~,~/l,:V
~/~J'R'
/\H
CO,H
42· R - a-OH 44· R, - OH, R, - H
43· R - 8-0H
45· R, - H, Rl - OH
FIGURE 29. (contd,).

~jOH
o
~HJ
16
17 , OH
o
1094 R = D
1095 R = B
1096 R =A
RJy
55 R1 = A. R2 =H
56 R1 = B. R2 = Ac
R1
57 R1 = E. R2 =H
1097 R1 = 0, R2 = H
1098 R1 = B. R2 =H
1099 R1 = C, R2 =H
21
16 14
A=~
I 13
17
B=~
HO" I
FIGURE 30. Structures of oxepane diterpenes (55-57, 1097-1099) and their linear
precursor-like compounds (1094-1096) reported from Montanoa (Heliantheae).
CHAPTER 5
Biological Activity of Diterpenes
V.I. Introduction
Various biological activities (Table 13 [pp. 489-490]) have been reported for
plant diterpenes, principally from members of the Ericaceae, Euphorbiaceae,
Lamiaceae, and Compositae. Each of the major diterpenoid classes from this last
family will be discussed below in terms of its biological properties.
V.2. Linear Diterpenes

Linear diterpenes derived from geranylnerol, geranylgeraniol, and geranyllina-
1001 occur commonly within the Compositae. The most diverse group of linear
diterpenes is derived from geranylnerol and includes lactonic, oxepane, and
furanoid members as well as unicyclic and macrocyclic derivatives. In addition
to the previously mentioned Montanoa oxepane diterpene series, oxepanes and
lactones have been detected in Acanthosperum, Ichthyothere, Melampo-
dium, and other genera mostly within the Heliantheae.
For hundreds of years, a tea brewed from the leaves of Montanoa tomentosa
has been used medicinally to induce labor and as an antifertility agent (419,
382). The M. tomentosa extract possessed abortifacient, labor induction, and
menstruation induction effects (372, 297). Zoapatanol (55) appears to be the tea
component responsible for most of the activity (368). In addition to zoapatanol,
several other oxepane diterpenes (56, 57, 1097, 1098, 1099) and their
uncyclized precursors (1094, 1095, 1096) were isolated from this species.
Commercial interest in these compounds has led to the synthesis of analogous
structures sharing similar pharmacological properties (353).
V.3. Bicyclic Diterpenes

Grindelane normal-Iabdanes 185 and 188 isolated from Grindelia, Chryso-
thamnus, Solidago, and Haplopappus displayed significant antifeedant activ-
ity against the Colorado potato beetle (440) and the aphid Schizaphis graminum
486 5. Biological Activity of Diterpenes
(441). The anatomical distribution of grindelanes was examined in Grindelia

campo rum and the development of anatomically defined chemistries was traced
over time. This work led to the observations that most diterpene resin
accumulated on the plant surface and the quantity of accumulated cuticular resin
was positively correlated with the number of multicellular epidermal resin
glands (340).
Surface resin production in G. camporum and other resin-producing
xerophytic plants (e.g., Chrysothamnus, Gutierrezia and Xanthocephalum)
may serve at least three (not mutually-exclusive) functions: (1) when coating the
leaf surface, the resin makes the cuticle less permeable to water and thus reduces
water loss, (2) the resin coating increases the reflectance of the leaf surface
thereby reducing the amount of solar radiation penetrating the surface and,
consequently, lowering the internal temperature, and (3) the resin deters
herbivores and/or plant pathogens (340).
Although the plant source, Nicotiana glutinosa, is a member of the
Solanaceae not the Compositae, the major leaf-surface-resin normal-Iabdane
constitutents, sclareol (1102) and 13-epi-sclareol, either have been isolated from
the Compositae (sclareol) or resemble other normal-Iabdanes isolated from this
family. When tested against a variety of fungi, these Nicotiana compounds
significantly inhibited the radial growth rate of common fungal colonies. Radial
growth was apparently retarded by the effect of diterpenes on the growth-
regulatory processes controlling fungal branching (24).
Solidago clerodanes are frequently referred to as the "bitter principal"
responsible for the characteristic taste of the root tissue. For example,
solidagonic acid (500) was described as a bitter principle from the roots of
Solidago altissima (365).
V.4. Tricyclic Diterpenes

When each of the diterpene resin acids, pimaric acid, dihydropimaric acid,
sandaracopimaric acid, isopimaric acid, neoabietic acid, levopimaric acid,
palustric acid, and abietic acid (Figure 31 [po 491]) was included in the artificial
diet of the pink bollworm, Pectinophora gossypiella, larval growth was
inhibited. In order to ascertain the importance of the compounds' C-19 acid
function in growth inhibition, methyl isopimarate and isopimarol, (Figure 31)
were tested under the same conditions and found to be substantially less active
than the free acid. Isopimarol had virtually no effect on larval growth.
Resemblance of the tricyclic diterpene skeleton to the ABC-ring system of
common steroids prompted the suggestion that the diterpenes interfered with the
pink bollworm's steroid metabolism. Insect hormones are produced from dietary
phytosterols which are absorbed, transported, and biochemically altered.
Interference by the diterpene resin acids at any stage of this process could
significantly reduce larval viability. To test this hypothesis, feeding studies were
conducted using a levopimaric acid test diet with added cholesterol (addition of
Tetracyc1ic Diterpenes 487
cholesterol diminishes the insect's requirement for phytosterols). In comparison

to the control diet that contained 0.2 percent levopimaric acid and no
cholesterol, test diets containing levopimaric acid and steadily incremented
cholesterol concentrations from 0.05 to 1.0 percent produced corresponding
increments (increases) in larval growth. By 1.0 percent cholesterol, the larval
weight had reached 86 percent of larvae grown on an artificial diet containing no
levopimaric acid, suggesting that added cholesterol canceled the deleterious
effect of the diterpene. It was concluded that reduced larval growth resulted from
the antagonism between resin acids and steroids and that the insect's hormonal
system was affected (258).
V.5. Tetracyclic Diterpenes

Feeding tests using kaur-16-en-19-oic acid (625) and trachyloban-19-oic acid
(791) from the florets of sunflower (Helianthus annuus) varieties resistant to
the sunflower moth, Homoeosoma electellum, produced significant reduction
in this insect's larval growth (491). Resistance of these varieties to seed
predation by the sunflower moth was attributed to the relatively high
concentration of these compounds in the sunflower's seed-bearing florets.
Further studies (332) showed that when other Helianthus diterpenes, ciliaric
acid (792) and angelylgrandifloric acid (649), were incorporated (one percent) in
the diet of sunflower moth larvae, the larvae experienced a significantly higher
level of mortality than those larvae feeding on the diet lacking the diterpenes.
The compounds did not affect the length of the development period but did
appreciably reduce the size of seven-day-old larvae.
Kaur-16-en-19-oic acid (625) obtained from Mikania monagasensis inhibited
the growth of Staphylococcus aureus and Candida albicans (384). In the latter
case, this diterpene was appreciably less active than the co-occurring sesquiter-
pene lactone, mikanolide.
Diterpenes of Wedelia (Heliantheae) were responsible for this plant's toxicity
to sheep and cattle. The first of two kaurenoid glycosides, wedeloside (679) and
atractyloside (681), caused the severe loss of sheep in Queensland, Australia,
due to grazing on Wedelia asperrima (408), while the second proved fatal to
South American cattle grazing on W. glauca (456). Investigation of W.
buphthalmijlora, another South American shrub toxic to cattle, (using
extraction methods unlikely to isolate kaurenoid glycosides), revealed a complex
chemistry consisting of kaur-9(l1), 16-dien-19-oic acid (690), kaur-16-en-19-oic
acid (625), and a variety of grandifloric acid (646) esters (455). One of these
esters, 15a-tiglinoyloxy-kaur-16-en-19-oic acid (650), isolated from W. scaber-
rima was miracidal (toxic to the miracidia stage of Schistosoma mansoni).
Kaur-16-en-19-oic acid was molluscicidal against Biomphalaria glabata (476).
The sulfated glycoside, carboxyatractyloside (678), was reported from two
sources, Xanthium strumarium (232) and Atractylis gummifera (239). This
hypoglycemic compound strongly inhibits translocation of adenine nucleotides
across the mitochondrial membrane and shows an in vivo toxicity ten times
greater than that of atractyloside (681, which co-occurs in A. gummiJera)
(239). Carboxyatractyloside was responsible for cocklebur poisoning of pigs in
the southern United States (238). Later work on the inhibitors responsible for
the dormancy properties of Xanthium seeds identified carboxyatractyloside as a
potent plant growth inhibitor (238).
Sweet-tasting ent-kaurene glycosides, stevioside (683), rebaudiosides A
(685), B (684), C, D (688) and E (689), dulcoside A (686), and steviolbioside
(682) (See Figure 21), have been isolated from the New World genus Stevia
(359, 464). Eighteen sweet-tasting Stevia taxa have been identified from the
total of 121 tested taxa (464). Stevioside, which is estimated to be three
hundred-fold sweeter than sucrose, is produced commercially as a sweetening
agent for desserts, soft drinks, sea foods, pickled vegetables, and so on.
Although no evidence indicates that stevioside is harmful to humans, the likely
hydrolysis product, steviol (Figure 32 [po 492]), is metabolized to mutagenic
structures by human enzymes and appears to covalently interact with DNA.
When steviol was incubated in the presence of rat-liver microsomes (S-9), the
principal metabolic product was 15a-hydroxy-steviol. Testing of this latter
compound did not reveal any mutagenicity. However, 15-oxo-steviol, a closely-
related derivative (Figure 32) was a direct-acting mutagen and a bactericide
(425).
The role of diterpenes in the resistance of four Solidago (Astereae) species to
the beetle Trirhabda (Coleoptera) is under investigation (368). Preliminary
results indicate that three of the four kauranoids isolated from the leaves of S.
nemoralis and S. altissima, ent-kauran-16a-ol (720), 15a-hydroxy-ent-kaur-
16-en-19-oic acid (646), and 17 -hydroxy-ent-kaur-15-en-19-oic acid reduced
Trirhabda larval growth by 40 percent and adult growth by 32 to 49 percent.
The fourth, ent-kaur-16-en-19-oic acid (625), had no deterrent effect on the
larvae and actually stimulated feeding by adults.
The diterpene alkaloids, lycoctonine (1009) and anthranoyllycoctonine (1010)
appear to be responsible for the blood pressure depressant, smooth muscle
relaxant and curare form properties of the source plant, Inula royleana (34).
Table 13. Plant Diterpene Biological Activities 489
TABLE 13. Plant diterpene biological activities.
Activity Compound Source Family Reference

Antifeedant
ajugarin I-III Ajuga remota Lamiaceae 305,306
grindelanes Chrysothamnus Compositae 340
nauseosus
Grindelia (7 spp.) " "
Haplopappus sp. " "
ciliaric acid Helianthus sp. " 306
kalmitoxins Kalmia latifolia Ericaceae 259
grayanotoxins " " " "
kaurenoic acids Helianthus ~ Compositae 258,306
trachylobanic " " " " "
acids
kaurenoid Wedelia spp. Compositae 408,455,456
glycosides
Xanthium strumarium " 238
Atractylis gummifera " 239
teucjaponin A Teucrium japonicum Lamiaceae 304
Antifungal
casbene Ricinus communis Euphorbiaceae 261
pseudolaric acid Pseudolarix Pinaceae 306
kaempferi
sclareol,etc. Nicotiana Solanaceae 24
glutinosa
Fish poison
eremone Emerocarpus 304
setigerus
hautriwaic acid " "
Insecticidal
ajugarin IV Lamiaceae 305
Molluscicidal, etc.
kaurenoic acid Wedelia scaberria Compositae 476
esters
Antibacterial
longikaurins Rabdosia longituba Lamiaceae 306
kaurenoic acid Mikania Compositae 384
monagasensis
TABLE 13. (contd.).
Activity Compound Source Family Reference

Antibiotic
przewaquinone Salvia przewalskii Lamiaceae 304
sonderianol Croton sonderianus Euphorbiaceae 305
Antimicrobial
7, 18-dihydroxy- Iboza riparia Lamiaceae 304
sandaracopimaradiene---
Curare form
lycoctonine,etc. Inula royleana Compositae 34
Antiviral
bacchotricuneatin Baccharis tricuneata " 490
Oxytocic
zoapatlin, etc. Montanoa tomentosa " 297,372
Plant growth inhibitor
podolactone Coniferae spp. Coniferae 304
carboxyatrac- Xanthium strumarium Compositae 238
tyloside
Sweetening agent
kaurenoid Stevia (18 spp.) 464
glycosides
Figure 31. Diterpene Resin Acids 491
15 16
Pimaric Acid 15,16db Sandaracopimaric Acid
Dihydropimaric Acid
Isopimarol R
Isopimaric Acid R = C02 H Neoabletic Acid
Methyl Isopimarate R = C02 Me
Levopimaric Acid Palustric Acid Abietic Acid

FIGURE 31. Diterpene resin acids tested for biological activity against pink bollworm
(Pectinophora gossypiella) larvae.
H OH
20
3 15
Stevioside R1 = Glu, R2 = H, R3 = OH
OH OH
Steviol R = H 15-0xo-steviol
15a-Hydroxy-steviol R = OH
FIGURE 32. Stevia diterpene, stevioside, its aglycone, steviol, and a mutagenic
derivative, 15-oxo-steviol.
CHAPTER 6
Diterpene Analysis with Emphasis on

Clerodanes
VI. 1. Clerodanes
VI.1.l. Major Clerodane Types
VI. I. I. I. trans-ent-Clerodanes (50'., IO(3-trans-Clerodanes)

Early work on Compositae diterpenes focused on Solidago and the normal-
labdane, solidagenone (Figure 33 [pp. 513-514]; Structure 158) (9, 16, 17).
Later, ent-derodanes (kolavanes) were found to co-occur with the labdanes
(364, 365). The first identified novel derodane, solidagonic acid (Figure 33;
Structure 500), was shown by chemical interconversion (364, 365; Figure 33) to
share the orientivity of the major chiral centers, C-5, C-8, C-9, and ClO, with
the co-occurring derodanes of known stereochemistry, kolavenic acid (495) and
kolavenol (Figure 33; Structure 475).
Structural correlation of solidagonic acid with 495 and 475 was made feasible
by the recent assignment by Misra and coworkers (391) of absolute stereo-
chemistry to the chiral centers of the Hardwickia pinnata derodanes, (-)-
hardwickiic acid (511), kolavenic acid, and kolavenol (Figure 34 [po 515]).
Their pivotal work on clerodane stereochemistry proceeded as described below:
1. Chemical degradation of 511 led to a series of products that permitted
assignment of the ring fusion configuration. The CD spectrum of derivative
511e produced a strong Cotton effect which was almost a mirror-image of
that produced by the steroid, 3/3-hydroxy-5a-androstan-17-one. This sug-
gested that the two rings of S11e were trans-fused, but with an absolute
stereochemistry opposite to that of the steroid's CD rings.
2. Orientivity at C-9 was established from the 511d IH-NMR data which failed
to indicate a shielding effect of the C-9 carbomethoxy group on the C-5
methyl. An a-oriented carbomethoxy group would have a 1,3-diaxial
relationship with the C-5 methyl which would then be subject to deshielding.
The absence of de shielding indicated a /3-oriented sidechain and an a-
oriented methyl at C-9.
3. The paramagnetic IH-NMR chemical shift (01.19) of the 511f C-8 methyl
signal (H-17) relative to the shift observed for the parent compound and
related structures (c. 00.83) was attributed to the de shielding influence of the
494 6. Diterpene Analysis with Emphasis on Clerodanes
keto group. Misra argued that since a carbonyl group can deshield only those
protons that lie in its plane, the C-S methyl must be equatorial (a-oriented).
The absolute stereochemistry of kolavenic acid and kolavenol follow from
their relationship with (-)-hardwickiic acid (391).
Unfortunately, the early assumption of (-)-hardwickiic acid-based biogenetic
uniformity among diterpenes of related Solidago species led to several incorrect
stereochemical assignments: Anthonsen and McCrindle (18) isolated from
Solidago elongata a series of clerodanes that co-occurred with kolavenol,
kolavelool (479), kolavenic acid plus several angelate and acetate ester
derivatives (480, 495, 498). Based on 1 H-NMR data that paralleled those of the
kolavane series, this new series of five clerodanes, elongatolides A-E, were also
assigned trans-ent-clerodane absolute stereochemistries (Figure 35 [pp. 516-
517]). Two other clerodanes from S. shortii (556 and 557) were assigned the
same stereochemistry (9).
Diterpenoids from S. altissima, first identified as a series of trans-ent-
clerodanes, solidagolactones I-VI (413), were in some instances identical to
members of the previously reported elongatolide series (Figure 35). Solidagolac-
tone (Figure 35; Structure 543), the only member of this series lacking a C-6
oxygen function, was shown via reduction/methylation to be identical to a
kolavenic acid derivative. Consequently, the absolute stereochemistry of the
kolavanes was assigned to 543 as well as the other six S. altissima clerodanes,
solidagolactones II-VII.
Co-occurrence with (-)-hardwickiic acid of known absolute stereochemistry
(391) also led to the assignment of its stereochemistry to the clerodane
constituents of S. juncea (318).
VI.l.l.2. cis-normal-Clerodanes (5a, 10a-cis-Clerodanes)
The first non-trans-fused clerodane (235) from the Compositae was identified
by X-ray as a C5a,ClOa-cis-clerodane, gutierolide (270). Perhaps prompted by
this finding and the growing number of such cis-clerodanes reported from other
plant families, the absolute stereochemistries of the next reported pair of
Solidago clerodanes (15), solidagoic acids A (239), and B (244), and a related
series of neutral clerodanes (317) were studied exhaustively. These structures
were assigned a 5a,lOa-cis-ring junction indicating a normal-Iabdane origin.
Initially, an attempt was made to correlate structure 239 with the established
stereochemistry of (-)-hardwickiic acid (511; Figure 36A [po 51S]). Chemical
conversion of 239 to 239a and the corresponding conversion of 511 to 507
permitted the comparison of the properties of the two constitutionally equivalent
derivatives, 239a and 507. Significant differences in their 1 H-NMR chemical
shifts proved the nonequivalence of the two parent structures, 239 and (-)-
hardwickiic acid (Figure 36A).
Attempts were then made to correlate 239 with a cis-clerodane of known
absolute stereochemistry [revised as per 15], plathyterpenone (1075). Compari-
son of the CD results for 239b (a derivative of 239) and 1075 suggested a cis-AB
ring-fusion at C-5 and C-lO identical to the revised 1075 (Figure 36B [po 518]).
Clerodanes 495
The Solidago shortii clerodanes reported initially as trans-ent-clerodanes

(See above) were reinvestigated (386) as part of the S. arguta study. Preparation
of the 3,4-iJ-epoxide of Sa, lOa-cis- fused solidagoic acid A produced a structure
with 1H-NMR properties strikingly similar to those of a S. shortii compound,
556. It was then suggested that this and other S. shortii structures be revised to
the corresponding cis-normal-clerodanes.
Reinvestigation of the above-mentioned Solidago elongata and S. altissima
C-6 oxygenated clerodanes was also prompted by the identification of
tricyclosolidagolactone (Figure 37 [po 519]; Structure 947), a cis-normal-
clerodane (5a,lOa-cis-fused) from S. altissima (500). This tricyclic clerodane
contained a cis-fused AB ring system. Niwa and Yamamura proposed that the
biogenesis of 947 (Figure 37) involved a precursor that was constitutionally
identical to the first-proposed structure for solidagolactone V (Figure 35;
Structure 262) but belonging to the cis-normal-clerodane class (402). They
reinvestigated the S. altissima clerodanes in order to resolve this inconsistency.
Consequently, the structures of solidagolactones II-VII and the corresponding
elongatolides were revised to cis-normal-clerodanes (Figure 35). Confirmation
of the absolute stereochemistry of the solidagolactone series was provided by X-
ray analysis of the C-6 p-bromobenzoate derivative of desacylsolidagolactone
VIII (401).
VI. 1.1.3. cis-ent-Clerodanes (5iJ,IOiJ-cis-Clerodanes)

A Solidago arguta report identified a mixture of seven clerodanes, one trans-
ent-clerodane (507) and six noveI5iJ,lOiJ-cis-ent-clerodanes, 578-583 (7). The
absolute stereochemistry assigned these structures was confirmed by X-ray
analysis (263) and by chemical interconversion (386). First, a nonheavy atom
X-ray analysis of 583 established its relative stereochemistry (Figure 38 [po
519]). The lactone 583 was transformed through reduction and acetylation into
the co-occurring compounds 581 and 582, respectively. Then, a study of optical
data for S. arguta compound 578 (Figure 39 [po 520]) confirmed the absolute
stereochemistry for these structures as well as other compounds of similar
properties. Haplopappic acid (576), isolated from Haplopappus angustijolius
and H. Joliosus (462), and the series of cistodioic acid-related structures from
Cistus monspeliensis (Cistaceae; 33, 469) were correlated through a series of
derivatives with these Solidago structures of established stereochemistry
(Figure 39).
CD (circular dichroism) and other optical data indicated that haplopappic
acid, the S. arguta clerodanes and the cistodioic acid-related structure series had
a common relative configuration that was largely opposite that of solidagoic acid
A (239) and B (244). The two enones, 576c and 578b, derived as indicated in
Figure 39 have positive Cotton effects for the n ---> 71"* transition of almost
identical molecular amplitudes (a + 65 and + 64, respectively). The two enones
derived from solidagoic acid A had an opposite and weaker Cotton effect (a -
46 and - 33) compared to those observed for 576c, 578b and related structures.
Despite opposite orientations at C-5, C-9, and C-lO, 5(J,1O(J- and 5a, lOa-cis-
clerodanes are epimeric rather than enantiomeric because both have a-methyls at
C-S.
VI.l.l.4. trans-normal-Clerodanes (5(3, IOex-trans-Clerodanes)

Of the four possible AB-ring junction orientations, three are well-documented
among the clerodanes of the Compositae. Identification of the fourth, a 5(J, lOa-
trans-normal-clerodane, is at best tentative. In the first report of trans-normal
clerodanes, structures 236 and 237 from Bedfordia sa/icina were illustrated
(122) without specifying orientation of the methyl groups (Figure 40 [po 521]).
Although constitutionally identical to kolavenol (475), 237 differed in its
spectral properties. In particular, the optical rotations for 237 and 475 were
opposite ([a]D = +7.9 and [a]D = -57.1, respectively, 365). The authors
suggested that the data for 236 and 237 were consistent with structures bearing
C-5(J-, C-S(J-, and C-9(J-oriented methyls. Nevertheless, the positive optical
rotation and methyl chemical shifts (e.g., 237: H-17,00.79; H-lS,01.69; H-
19,01.05; H-20,0.S2) for 236 and 237 are also consistent with the cis-ent-
clerodanes (Table 14 [pp. 507-510]).
Koanophyllon admantium compounds 245 and 250 were depicted as trans-
normal-clerodanes with (J-oriented C-S methyls (Figure 40; 42). However, the
structures were accompanied by the statement that the absolute configuration of
these diterpenes was not determined, raising the possibility that 245 and 250
were (-)-hardwickiic acid and its 1,2-dehydro-derivative, respectively. The
Koanophyllon clerodanes shared with (-)-hardwickiic acid a negative optical
rotation. The confusion regarding these structures was heightened by the report
of these two structures from Centipeda (128) and 251, the methylester of 250,
from Nidorella (72) in which the structures were displayed with C-8a-methyls
(The C-8a-methyl epimers of 245 and 250 are treated here as 249 and 248,
respectively). Although 251 was reported as a methylester (nidoreseda acid
methyl ester) from Nidorella, when this structure report was cited in the
Centipeda article the structure was described and drawn as the free acid.
The Centipeda compound 249 assignment was based on correlation with the
Solidago (286) trans-ent-clerodane, (-)-hardwickiic acid. The discrepancy
between the structure illustrated for 249 and that of (-)-hardwickiic acid was not
discussed. Possibly, the above-described confusion results from incorrectly
illustrated structures for 248,249, and 251. Because 249 was described as being
previously reported by Misra et al. (391), it is assumed that this structure is
actually (-)-hardwickiic acid and is probably identical to 245. The other
structures, 248 and 250, are presumably the same compound and identical to
1,2-dehydro-(-)-hardwickiic acid. Very likely, 248 and 249 are the same as 250
and 245, respectively.
A previously characterized clerodane, 238, and two novel clerodanes, 253
and 254, were reported as 5{J,lOa-trans-clerodanes from Nidorella (72). The
citation for the known compound was a Solidago article (317) in which the
Clerodanes 497
structure was drawn differently (as 1064, a 5a,lOa-cis-clerodane). Structures

238 and 1064 differ in that their C-5 hydroxymethylenes are {3- and a-oriented,
respectively (Figure 40). The authors noted that the absolute stereochemistry of
these compounds was not determined and that the displayed structures were only
tentative. Possibly, the authors intended all three of these structures (238, 253,
and 254) to be shown with the more common configuration of 1064.
Based on the above-described reports, there is no well-established example of
5{3,lOa-trans-clerodanes in the Compositae.
The previously mentioned mix-up regarding the Nidore/la compounds has
exacerbated an already confused situation regarding the name(s) and structure(s)
proposed for the 5,1 O-seco-clerodane structures. The first report of a compound
with these properties from Conyza stricta (460) incorrectly assigned the
structure of ,::ll-polyalthic acid (Figure 40) to the compound, conyzic acid. A
second compound, secoreseda acid, from Nidore/la resedifolia (72) (Figure 40)
was assigned a relative (but not absolute) stereochemistry, based on analogy
with co-occurring compounds. Concurrently, a diterpene isolated from Conyza
stricta, strictic acid, (470) was assigned a structure epimeric at C-9 to that first
proposed for secoreseda acid. Comparison of the properties of these three
compounds led to the subsequent proposal that conyzic acid, secoreseda acid,
and strictic acid were identical (376) and that the probable structure was that of
secoreseda acid (Figure 41 [po 522]; Structure 2). The C-9 methyl was assigned
a {3-orientation because secoreseda acid co-occurred with compounds with {3-
oriented C-9 methyls. Later, when secoreseda acid was reported from Conyza
scabrida, the structure was drawn as a trans-ent-clerodane derivative (Figure
41; Structure 3; 83). The assigned stereochemistry was at least in part based on
the co-occurrence with biogenetically closely related trans-ent-clerodanes (see
Figure 11). This revision of the secoreseda acid structure was published without
comment by the authors (83). However, this revised version has the same
absolute stereochemistry as that originally assigned to strictic acid (470) and is
currently the best guess at the structure of conyzic acid/strictic acid/secoreseda
acid.
VI.l.2. I H-NMR Spectrometry of Clerodanes

As suggested by the preceding discussion, assignment of orientivity at the four
clerodane asymmetric centers, C-5, C-8, C-9, and C-lO, is likely the most
problematic aspect of structure elucidation. The co-occurrence in the same
species of clerodanes representing different ring-junction types erodes the
reliability of biogenetic arguments in assigning stereochemistry based on
stereochemical properties of compounds previously isolated from the same
species or from related species. Given the range of biogenetically feasible
structure candidates, assignment of stereochemistry may require choosing
between pairs of enantiomeric structures or between constitutionally identical
structures that are epimeric at one or more centers. Such a problem greatly
complicates the assignment of absolute stereochemistry.
VI.l.2.1. General Properties of Methyl Chemical Shifts

A reference point for the evaluation of the I H-NMR chemical shifts of the
clerodanes is the study initiated by Zurcher on the steroid I H-NMR properties.
Zurcher examined the effects of individual substituents on the chemical shifts of
the C-lO and C-13 angular methyls of the four androstane skeletal types (504,
505; Figure 42A [po 523]). His findings became codified as the "Zurcher
Rules. " Chemical shifts for the four reference compounds (Figure 42A)
demonstrate that angular methyl shift values depend in part on the cis or trans
nature of the ring junction.
Other results indicate that the largest deshielding effect on angular methyls
results from substituents that have a I ,3-syn-diaxial relationship with the methyl
group. Comparable substituents that are equatorial at these positions have little
influence on the methyl chemical shifts. In general, substituents on carbons that
are vicinal to the methyl-bearing ring carbon display the second greatest
deshielding influence.
Similar patterns can be observed in the constitutionally equivalent representa-
tives of the three clerodane types (Figure 43 [po 524]):
1. The 5a,1O,8-trans-representative (Figure 43; Structure C-1) with its trans-

AB ring junction and the syn-diaxial arrangement of the C-9 and C-5 methyls
is comparable to the 5a-14a-androstane structure (Figure 42A; Structure 1):
Its relatively upfield C-5 and C-9 methyl chemical shifts are largely a
consequence of the methyls's axial relationship to the ring system.
2. The introduction of the A-B and/or C-D cis-ring junction into the last three
representative androstane skeletons results in an appreciable downfield shift
of the angular methyl situated at the cis-junction. Relative to the 5a-1O,8-
trans-clerodane structure, C-5 methyls of both the 5a,lOa-, and 5,8,1O,8-cis-
representatives display similar downfield shift effects (Figure 43;
5a, 10,8:0 1.00; 5a, lOa:o 1.17; 5,8,10,8:01.06).
3. In both the 5a, lO,8-trans- and 5,8,1O,8-cis-clerodanes, the C-9 methyl adopts
an axial orientation that is trans to H -10. Both produce chemical shifts (00.74
and 0.84, respectively) that are up field from the shift of the equatorial C-9
methyl of the 5a,lOa-cis-structure (01.08). Despite the flexibility of the
5a, 10a-cis-decalin system, evidence (discussed below) suggests that for this
system the conformation with the C-9 equatorial methyl is generally favored.
The usefulness of I H-NMR chemical shifts in differentiating the two major
clerodane isomeric types (5a,1O,8-trans- and 5a,lOa-cis-fused) was first noted
in the comparison of the chemical shifts of the solidagoic acid A (239) derivative
(239a) and the (-)-hardwickiic acid (511) derivative (507) (Figure 36A).
Analysis of additional structures of the two isomeric types demonstrated that the
most useful I H-NMR parameters for assigning stereochemistry were the C-5-,
C-8-, and C-9-methyl chemical shifts. Niwa and Yamamura (402) observed that
the C-8-methyl doublet (00.90) of 239a appeared upfield from the C-9 methyl
singlet (01.08), while the C-9 methyl singlet (00.74) of 507 occurred upfield
Clerodanes 499
from the C-8 methyl doublet (00.86). These differences were attributed to the
presence of an equatorial C-9 methyl in 239a and an axial C-9 methyl in 507.
Based on examination of compiled C-4, C-5, C-8, and C-9 methyl chemical
shifts (Table 14), with very few exceptions the relative positions of C-8 and C-9
methyl chemical shifts observed by Niwa and Yamamura characterize all listed
compounds of the two major clerodane types.
VI. 1.2.2. 1 H-NMR Properties of cis-normal-Clerodanes

(5a, 10a-cis-)
VI.1.2.2.1. C-6 Oxygenation
The C-9 methyl (H-20) chemical shift generalization made by Niwa and
Yamamura (402) for the 5a, lOa-cis-clerodanes seems to be consistent for all
compounds listed in Table 14. The compounds with the most divergent H-20
chemical shifts, 262 (01.21), 265 (01.17), and the synthetic product 262a
(01.24) (402), represent all the listed structures with C-6 keto functions. While
no H-20 deshielding is evident for C-6 hydroxyl- or ester-containing structures,
such deshielding is pronounced for the C-6 carbonyl-bearing compounds (Figure
44 [po 525]).
VI.1.2.2.2. Conformational Variability

I H-NMR data support the view that two basic conformations, I and II, (or some
minor variant of lor II in which, for example, the A-ring exists as a flattened
half-boat form or some twist analog) occur within the 5a-lOa-cis-clerodanes
(Figures 45A [po 526] and 46 [po 527]).
Individual circumstances tend to favor one conformation or the other. For
instance, the presumed conformation for hemiacetal or lactone ring-containing
compounds with C-18, 19-oxido linkages (Figure 45B [po 526]) is conformation I
because the closure of the hemiacetal or lactone ring imposes less constraint on
the decalin system in this conformation. Compound 1068 (Figure 45B) is
characterized by a H-3 lH-NMR signal that is relatively narrow (W1/2 = 3Hz),
in agreement with the proposed conformation (317). However, as will be
described below not all such C-18,C-19-heterocyclic structures agree with this
interpretation.
The assignment of conformation was more problematic for compounds
lacking C-18,19-oxido linkages. Based on a variety of data (15), Anthonsen and
coworkers proposed that conformation II with the A-ring flattened into a half-
boat was more reasonable than conformation I. They argued that their proposal
was supported by the C-9 methyl (H-20) chemical shift for compounds with the
A-ring substituents shown in Structure 4 of Figure 45A. As drawn, the C-9
methyl is directed over the enone function and is shielded by it. In compounds
lacking the enone, the methyl produces a signal at approximately 01. 05.
However, when the enone is present the methyl signal appears at about 00.85
(15).
These results, in particular those for structure 239b, suggest that the shielding
zone of the ketone (in the absence of a,{3-unsaturation) alone is sufficient to
cause the observed H-20 chemical shift. Other examples of this shielding effect
include structures 239d, 239b, and 239c (Table 14; Figure 60 [pp. 541-544]).
A derivative, 263a, prepared from a variety of sources (solidagolactones II
and III and 263) by Goswami and coworkers, displayed methyl chemical shifts
(Table 14) that were inconsistent with the above-described shielding effect
(291). In depicting the conformation of the related structures 268 and 269,
Goswami and associates (291) opted for the conformation that was most
consistent with their results (Figure 45C [po 527]). As in conformation I, the C-9
methyl was equatorial, and the C-6 ester was axial.
The results reported by Anthonsen and coworkers (15) and Goswami and
associates (291) appear on the surface to be contradictory. However, these and
other results (described below) are made compatible by assigning the favored
conformation according to "rules" based on several alternative A and Bring
substitutional patterns. If R, (Figure 46) is a keto function and R2 is a pair of
hydrogens, then conformation II is favored. However, the results suggest that if
R2 is an oxygen substituent the favored conformation is I regardless of the R,
substituent. Given that the majority of 5a, lOa-cis-clerodanes have C-6 oxygen
substituents, the most common conformation is expected to be I. If R2 is a keto
function, maximum deshielding of the C-9 methyl is expected in conformation I
(or some minor variant of this conformation). This effect is pronounced in the C-
9 methyl chemical shifts of 262, 262a, and 265 (51.21, 1.24, and 1.17,
respectively) .
These "rules" are consistent with the data reported by Goswami and
coworkers (291) and with data reported for the two structures, 1066 and 244a,
(Figure 47 [po 528]). However, not all results are consistent with the
generalization that conformation I should be favored in structures bearing a C-
18,C-19-heterocyclic ring. The comparison of the methyl chemical shifts for
1066 and 244a indicate a sizable difference in the chemical shifts of H-20 (51.03
and 0.84, respectively, Figure 47A). Partly, this difference can be attributed to
the occurrence of the tetrahydrofuryl moiety in 244a and the furyl moiety in
1066. However, comparison of similar structures differing in this manner
(Figure 47B) reveals that the deshielding effect of the furyl moiety on H-20 is
approximately 50.07-0.08 greater than that of the tetrahydrofuryl moiety. The
difference in H-20 chemical shift between 1066 and 244a, 50.19, suggests that
some factor other than the furyl moiety is contributing to this difference. The
only other structural difference is the C-2 keto function. If the C-2 keto group is
responsible for this evident shielding effect of H-20, then conformation II is
plausibly assigned to 244a. This result is consistent with the proposed "rule"
that if R, = 0 and R2 = H,H (Figure 46) then conformation II is favored.
The "rules" for the interpretation of conformational variability are further
supported by the data for the two 1025 conformations detected at - 50°C
(Figure 48 [po 529]; 170). While the room temperature CDCh spectrum was
difficult to interpret, two distinct sets of signals were obtained at - 50°C. The
Clerodanes 501
first (1025a; Figure 48) was characterized by a B-ring conformation in which the
C-6 acetate adopted an axial position and the C-9 methyl was equatorially
oriented. This corresponds most closely to conformation I described above. The
C-9 methyl chemical shift (00.93) is in agreement with this equatorial position.
In the second conformation (1025b; Figure 48), the C-6 acetate adopts an
equatorial orientation and the C-9 methyl is axially oriented (conformation II).
The upfield position of the C-9 methyl signal (00.73) is consistent with the
shielding effect of the C-2 keto on the axial methyl. These assignments are
corroborated by the H-6 coupling constants. For 1025a, the H-6 signal appears
as a broad singlet, while the H-6 signal for 1025b is a doublet (J = 12Hz), values
which are consistent with the proposed conformations. In compliance with the
above' 'rules," this structure which possesses a C-6{1-oxygen substituent adopts
conformation I as the dominant conformation at room temperature (Figure 48).
Several other lines of evidence were developed for the assignment of
conformation I to C-6 oxygen-substituent-bearing structures. In the first,
Eu(dpmh-induced shift results for C-6 hydroxy-representatives of 5{1, 1O{1- and
5a-lOa-clerodanes supported the two conformations indicated in Figure 49 (p.
530). The normalized ratio for the 5{1, lO{1-fused structure (Figure 49; 386) was
interpreted as support for a steroidlike conformation. The C-19 value for the
Sa, lOa-fused structure (5.3) was indicative of an anti-trans relation of C-19 to
the axial C-6 hydroxyl and of a nonsteroidal conformation (378).
The second line of evidence was based on the chemical transformations of 545
to yield two products, 545a and 545b (Figure 50 [po 531]). The formation of a
compound with an ether bond between C-3 and C-6 (545b) was considered proof
of a Sa, lOa-cis-ring junction and a nonsteroidal conformation (378).
Vl.l.2.2.3. 3,4-Epoxides
The 3,4-epoxide functions of c1erodanes can adopt either an a- or {1-oriented cis
configuration. As this represents one more complication in the already difficult
task of assigning absolute stereochemistry, it is not surprising that epoxide
orientation within the elongatolide (solidagolactone) series of 5a,lOa-cis-
c1erodanes has been misassigned. Elongatolides D (solidagolactone VI, 413;
553) and E (solidagolactone VII, 413; 260) were the first reported 3,4-epoxide-
containing c1erodanes of this type (currently accepted structures shown in Figure
51A [po 532]). Although they were initially described as trans-c1erodanes with
unspecified epoxide orientation (Figure 35; 18), Niwa and Yamamura (402)
revised these structures to Sa, 10a-cis-clerodanes with a-epoxides (Figure 51).
Their assignment was based on a series of transformations involving the furyl
derivative of 260 (Fig. SIB [po 532]). They argued that the formation of 260b
and 260c suggested that the C-4 tertiary hydroxyl group must be axially oriented
which would be compatible with the original presence of an a-epoxide ring in
260. However, the conformational flexibility of the Sa, lOa-clerodane skeleton
provides a variety of reasonable conformations: In the instance of the C-4 a-
hydroxyl, conformations with either the axial or equatorial configuration of this
functionality can reasonably be proposed. Likewise for the C-4 {3-hydroxyl

option, there are two possible orientations (axial or equatorial).
The structural questions relating to 553 and 260 were finally resolved by
Nishino et al. (401). Epoxidation of solidagolactone IV (545) yielded (in order
of abundance) two products, the {3- and a-epoxides (Figure 52B [po 534]). The
observed ratio of products was in agreement with the usual mechanism for the
epoxidation of homoallylic alcohols: In the presence of a C-6 {3-0H group, the
epoxide of the major product should have the same configuration as the hydroxyl
group. Data for the major product ({3-epoxide) included an IR absorption at 3470
cm - 1 (unaffected by dilution) indicative of hydrogen bonding and no absorption
at 3600 cm - 1 which, if present, would suggest a free OH. The IR spectrum of
the minor product (a-epoxide) included an absorption at 3600 cm - 1 and only a
weak absorption at 3475 cm- 1 which was affected by dilution. Further evidence
for the hydrogen bonding of the epoxide oxygen and the C-6 hydroxyl was the
presence in the 1H-NMR spectrum of the {3-epoxide-containing structure of a
sharp singlet at 05.41 (OH proton), whereas the OH proton of the a-epoxide
occurred as a multiplet at approximately 01. 8. Because this intramolecular
hydrogen bonding is only possible if the 3,4-epoxide is {3-oriented, the major
product was assigned this configuration. The {3-epoxide was correlated with
solidagolactone VII (260) and VIII (988) by a set of reactions (Figure 51C [po
533]) in which 260 and 988 and the p-bromobenzoate derivative (Figure 51C;
Structure 5), were transformed to the corresponding furyl derivatives and
through hydrolysis to the common product (Figure 51C; Structure 4). More
importantly, the other compounds were correlated with the p-bromobenzoate
derivative (Figure 51C; Structure 5) for which X-ray analysis provided the
absolute configuration. Consequently, the a-epoxide structure proposed for
solidagolactone VII (and presumably solidagolactone VI) was revised to a {3-
epoxide.
An unexpected result of the study by Nashino and his coworkers was the ratio
of products in the solidagolactone IV epoxidation reaction (Figure 52B), 1. 7 ({3-
epoxide): 1.0(a-epoxide). Given that the homoallylic hydroxyl system should
favor an attack on the same side of the molecule as the hydroxyl function ((3), the
surprisingly nonskewed observed ratio suggests that in the absence of this C-6
hydroxyl, attack from the a-face of the A-ring is favored. Support for this
proposal came from an apparently unlikely source (291) in which just the
opposite assumption was made. Solidagolactones VII (260) and VIII (988) were
isolated by Goswami and associates from Solidago virgaurea and correctly
identified as 5a,lOa-cis-clerodanes. The epoxide was assigned an a-orientation
in agreement with the previously published findings of Niwa and Yamamura
(402). Treatment ofthe solidagolactone II (258) and III (259) mixture with m-
chloroperbenzoic acid yielded an angelate/tiglate pair of epoxide products that
were isomeric to 260 and 988 (Figure 52C [po 535]). The authors assumed that
this angelate/tiglate pair possessed a {3-epoxide because the H -3' s chemical shift
(03.04) and coupling constant (d, J=4Hz) were distinct from those (02.74,
broad singlet) of the naturally occurring pair of structures (260 and 988) to
which they had previously assigned an a-epoxide. However, the absolute
Clerodanes 503
configuration of solidagolactone VII was subsequently established and revised to

a ,6-epoxide (361). Given that Goswami and coworkers originally misassigned
the epoxide of 260 and 988, then the epoxide of the isomeric transformation
product (Figure 35C) must have just the opposite configuration (a) to the one
originally assigned (,6). The similarity of the 1H-NMR data for the H-3 proton of
the epoxidation product (d, J = 4Hz) and the a-epoxide synthesized by Nishino et
al. (d, J = 5.1Hz) supports this conclusion. The observation that this a-epoxide
was the major product (no other products were identified) suggests that in the
absence of the C-6 ,6-hydroxyl, epoxidation occurs most favorably from the a-
face. A similar epoxidation reaction (Figure 52D [po 535]) involving the C-6
acetate of solidagolactone IV (545, 413) yielded one detectable product
(probably an a-epoxide) characterized by a doublet H-3 signal with J =4.5Hz.
In another epoxidation reaction (Figure 52A), a transformation product of
solidagoic acid, 239, (15) yielded two epimeric epoxides (386). Differentiating
the two epimers was attempted by the further transformation of the ,6-epoxide
(Figure 53 [po 535]) (386). 1 H-NMR evidence of an axial (,6) hydroxyl function
at C-3 in the product of this Lewis acid treatment was used as evidence in the
assignment of spectroscopic properties to each epoxide. Two aspects of the
assignments appear contradictory to previously reported findings. First, the ratio
of products, 3(,6-epoxide):I(a-epoxide), indicates that in this instance attack
from the ,6-face of the 5a-lOa-cis-clerodane is favored. Second, the H-3
coupling constants reported for the two epimers are opposite those assigned by
Nishino et al. (Figure 52B). Accordingly, it appears that the two epoxide
products (Figure 52A) should be revised such that the major product is the a-
epoxide. However, caution should be exercised in concluding that the reaction-A
products are misassigned. There are several reasons for caution. The absence of
a C-6 oxygen function may affect the conformation of the products of reaction
A, with the result that coupling constants differ from those of C-6 oxygenated
compounds. Further, the effect of the absence of the C-6 function on the
likelihood of ,6-face attack during epoxidation is not well understood.
A recent definitive study of the stereochemistry of C-6 substituted 5a-lOa-cis-
clerodanes (483) confirmed the above interpretation of the results for the
epoxidation of the C-6 ,6-acetate and formally revised the epoxide configurations
(described above) originally assigned by Niwa and Yamamura (402) and
Goswami et al. (291). The authors also used a- and ,6-epoxide analysis results to
determine the feasibility of applying Tori equation calculations to the prediction
ofH-3 coupling constants (Figure 54 [po 536]). Dihedral bond angles for H3-C3-
C2-H,6-2 and H3-C3-C2-Ha-2 for the ,6-epoxide were known and those for the
a-epoxide were estimated based on an anticipated change of 18 0 in this angle
during epoxidation of the olefin. In each instance the calculated coupling
constants closely approximated the observed values.
VI.I.2.3. 1 H-NMR Properties of trans-ent-Clerodanes

The axial configuration of the C-9 methyl (H-20) results in a relatively high-field
1 H-NMR chemical shift for this signal. Departures from the typical value of c.
00.75 for H-20 can usually be attributed to the de shielding effect of an oxygen
function at one of several possible positions:
VI. 1.2.3.1. C-7a-OR

The 1H-NMR spectra of C-7a-hydroxyl-bearing compounds 509, 559, and 562
and C-7a-acetoxyl-bearing 500 and 509a produce H-20 singlets at 01.02,0.92,
0.86, 0.97, and 1.02, respectively (Figure 55 [po 537]). Spectra of compounds
509,500, and 509a display H-19 singlets at 01.36, 1.17, and 1.34, respectively.
The spectra of the C-7 keto derivatives of 500 and 509 are characterized by H-19
and H-20 singlets that are 00.2-0.3 upfield from the parent compounds (Figure
55). These observed chemical shifts are attributable to the 1,3 ,5-triaxial
relationship of the C-5 methyl, the C-9 methyl, and the C-7 a-hydroxyl or ester
function. The interaction between these substituents is shown in Figure 56 (p.
538) from data supplied by Ohsuka et al. (412).
VI.1.2.3.2. C-12-0R
The C-12 hydroxyl function is the probable cause of the relatively downfield
position of the H-20 singlet (00.94) in the spectrum of 1061.
VI.1.2.3.3. C-19-0R and Aldehyde
Introduction of a hydroxyl function at C-19 has minimal effect on the chemical
shift of H-20 (Table 14 and Figure 57 [po 539]). However, attachment of
increasingly bulky ester functions (e.g., angelate) at C-19 appears to result in
modest deshielding of H-20. Structure 904 which differs from the related
compounds 900,902,903, and 1033 (hautriwaic acid) (Figure 57) by the further
oxidation of C-19 to an aldehyde is characterized by an H-20 singlet at 00.60.
The considerable shielding of this methyl is attributed to the aldehyde (C-19)
which is 1,3 diaxially oriented with respect to the C-lO methyl (H-20).
VI.1.2.3.4. C-17 Aldehyde
Oxidation of the C-8 methyl (H-17) in compound 967 appears to have an
appreciable deshielding effect on H-20 (01.00).
VI.I.2.4. cis-ent-Clerodanes
McCrindle and coworkers (386) have proposed a conformation for the 5{3,10{3-
cis-clerodanes (Figure 58 [po 539]). The H-20 chemical shifts for the members
of this series (Table 14) are consistent with the depicted axial arrangement for
this methyl. A comparison of the values reported for the cistodioic acid series of
compounds (Figure 59 [po 540]; 33, 469) and those of the Compositae (Table
14) suggest that the range of observed C-9 methyl chemical shifts results largely
from differences in the sidechain moiety. A saturated sidechain is correlated
with the relatively upfield values, while the furyl sidechain is associated with the
most downfield.
Vl.l.3. 13C-NMR Spectrometry of Clerodanes

Reviews of diterpene 13C-NMR data have focused in one instance on all reported
diterpenes (494), in the second instance on the trans-clerodanes (375), and in
Tricarbocyc1ics 505
the third (378), on the use of these data to differentiate between 5ex, Wex-cis- and
trans-c1erodanes. As this third review deals specifically with the solidagolactone
problem, it will be discussed at length here.
Pendant methyl groups of c1erodanes display some of the same properties as
those previously elucidated for steroids (Figure 42; 504 and 505). Principally,
the configuration of the ring junction influences the chemical shifts of the
associated methyls. Comparison of the C-17, C-19, and C-20 chemical shifts of
a series of C6-substituted 5ex,Wex-cis-c1erodanes with those of several trans-
c1erodanes reveals differences consistent with those observed for cis- and trans-
decalin (Figure 42B) and steroid systems (Table 15 [pp. 510-512]; Figure 61
[pp. 545-549]). In the cis-c1erodanes, the C-19 signal appears in an area
centered on 025, while in the trans-c1erodanes it occurs between 017 and 19.
Similarly, the C-20 signal resonates at a lower field (021 to 29) than that of the
C-20 of the trans-c1erodanes (017 to 19). The C-17 signals of both cis- and
trans- fused compounds display relatively constant chemical shifts near 015.
The association between ring junction and methyl chemical shift was
attributed to the shielding effect from carbons with a T-gauche relationship to the
resonating carbon. In trans-c1erodanes, the number of carbon atoms having a T-
gauche interaction with C-19 is larger than the number in cis-c1erodanes. In
trans-c1erodanes, C-20 has an axial orientation, while in cis-c1erodanes, this
methyl has an equatorial orientation. The relatively constant chemical shift of C-
17 in trans- and cis-c1erodanes is attributable to its equatorial orientation in both
ring junction types (378). Evidently, C-19 and C-20 \3C-NMR chemical shifts
are useful in distinguishing cis- and trans-c1erodanes (Figure 61). Just how
useful these data will be depends on how many exceptions (if any) will be found
to the data in Table 15.
VI. 1.4. Conformational Analysis (X-ray)

Quantitative conformational analysis of trans-c1erodanes (256) and 5ex, Wex-cis-
c1erodanes (378) has been conducted on X-ray diffraction results.
VI.2. Other Bicarbocyclics

I3C-NMR studies of 1abdanes have focused in one instance on the normal-
1abdanes, manoyl oxide (272), manool (996), sc1areo1, and marrubiin (4), and in
a second on the C-2{j- and C-3a-hydroxylated ent-labdanes (424) reported from
a non-Composite, Phlogacanthus thyrsiflorus. The results of the first study
and other unpublished 13C-NMR findings for normal-Iabdanes were discussed in
detail by Wehrli and Nishida (494).
VI.3. Tricarbocyclics
Early I H-NMR work on the resin acids, sandaracopimaric, pimaric, isopimaric
acids and their dehydro- and tetrahydro- derivatives, applied chemical shift
calculation methods to the prediction of C-17, C-18, and C-20 methyl chemical
shifts (19, 20). 13C-NMR results for several other normal-pimaranes were
recently reviewed (494).
Investigation of 1H -NMR properties of the sandaracopimaranes isolated from
Garuleum and Osteosperum (156) led to the proposal of a conformation for
these structures in which the A-ring adopted a twist form (Figure 62 [po 550]).
Evidence for this conformation was provided by the comparison of the C-4{3-
methyl chemical shifts for sandaracopimar-15-en-8{3-01 and its C-6{3-hydroxy
and acetoxy derivatives (Structures 1, 3 and 4, respectively; Figure 62; Table
16 [po 512]). The C-6{3-hydroxyl group had a strong deshielding effect on the C-
4{3-methyl, an effect which was diminished by introduction of an acetyl group.
This effect agrees with the proposed 1,3-syn-diaxial relationship between the C-
6 hydroxyl and the C-4{3-methyl. The deshielding effect of ths C-6 hydroxyl on
the C-I0 methyl suggests that the same 1,3-syn-diaxial relationship exists for
these substituents. The introduction of a C-l1{3-hydroxyl group (Structures 11
and 12; Figure 62) displayed the expected deshielding effect on the C-lO and C-
13 methyls (Table 16). However, equatorially oriented hydroxyl groups at C-ll
and C-12 (e.g., Structures 5, 7, and lO; Figure 62) had much less effect on
neighboring protons.
Detailed 13C-NMR results for ferruginol (319) and other aromatic abietane
compounds were used to indicate the stereochemistry at C-4 for compounds
possessing either an equatorial or axial carbinol group (494).
The only review of 13C-NMR results for the cassane series focused on a group
of compounds from a non-Compositae source (Caesalpinia bonducella) that
were substitutionally distinct from those reported from Osteospermum (231).
VI.4. Tetracarbocyc1ics and Related Skeletons

Pre-1978 13C-NMR analyses of ent-kauranes (357, 310, 309, 449) have been
reviewed (494). Another report (502) included complete data for the Stevia ent-
kaurene glucosides, stevioside (683), rebaudioside A (685), and paniculosides 1-
III (895-897). Recently, a detailed study of kaurenoic acid derivatives (345)
sought to compare the 13C-NMR chemical shifts of ent-kaur-16-en-19-oic acid
(625) with those of hydroxy derivatives at C-6, C-7, C-ll, C-12, and C-15 and
with kaurenolide. Another study (265) reported the results of complexation of
ent-kaurane polyols with boric acid. Compounds containing 1,2- orland 1,3-
glycol systems displayed boric acid-induced shifts in their 13C-NMR spectra
together with broadening of signals of carbons attached to or adjacent to the
glycol function.
ent-Beyerane and beyerene 13C-NMR data have been reported for a series of
C-l- and C-12-substituted structures (486, 494) and for a series of C-2- and C-3-
substituted compounds (308).
The 13C-NMR parameters for trachylobane and C-19 derivatives were
consistent with predicted values derived from 9-methyl-trans-decalin and
tricyclo[2.2.1.0 2 •6]octane (21).
Table 14. 'H-NMR Chemical Shifts 50?
TABLE 14. 'H-NMR Chemical Shifts (0) for the C-17, C-18, C-19, and C-20
Methyls of Clerodanes.
Compound
No. H-l? H-18 H-19 H-20
5a,10a-cis
1. 1025(RT)1 0.93 1. 95 1. 32 0.93

2. 1025b 1.04 1.18 0.73
3. 1025a 0.84 1.29 0.93
4. 239 2 0.89 1. 52 COOH 0.98
5. 239a 3 0.92 1.62 1.17 1. 08
6. 310 0.94 (4.24,3.96) (3.83,3.50) 1. 09
7. 258 0.86 1. 56 1. 28 1. 08
8. 259 0.85 1.56 1. 28 1. 08
9. 545 0.88 1. 70 1.15 1.03
10. 262 0.83 1. 50 1.17 1.21
11. 263 0.89 1.64 1.26 1.08
12. 265 0.84 1. 57 1. 30 1.17
13. 268(Ang)/ 0.86 0.98 1.33 1.10
269(Tig)
14. 261 0.88 1. 29 1. 21 1. 03
15. 260 0.88 1. 31 1. 22 1. 03
16. 260a 1. 03 (4.93-5.01) 1. 28 1.18
17. 262a 0.87 1. 54 1.24 1. 24
18. 260b 0.87 1. 08 1.16 1.16
19. 260c 0.86 1.23 1. 08* 1. 00*
20. 260d 0.85 1.26 1. 20* 1.03*
21. 263a 0.97 1. 37 1. 04
22. 1091a 0.93 COOH 0.91
23. 1091 0.92 COOH 0.89
24. 1085 0.98 (4.47,4.95) COOH 0.98
25. 1062( CC1 4) 0.78 1. 42 CHO 0.78
26. 1063( " ) 0.85 CHO CHO 0.96
27. 1064( " 0.90 1. 67 CH20H 1. 08
TABLE 14. (contd.).
Compound
No. H-17 H-18 H-19 H-20
28. 1065( " ) 0.85 (4.16) 1.18* 1. 03*
29. 1066( " ) 0.90 COOR (4.44,3.80) 1.03
30. 1067( " ) 0.85 (4.21) (5.42) 0.97
31. 1068( " ) 0.81 (4.89) -CHOH- 0.88
32. 1026 0.96 0.87 0.96 - CH 2-(1.58,1.69)
33. 556 0.88 1.23 1.11 0.94
34. 239b 0.87 0.97 1. 22 0.90
35. 239c 0.96 1.94 1. 28 0.83
36. 239d 1. 02 1. 95 1.27 0.90
37. 244a 0.82 COOR (4.43,3.88) 0.84
5a.,10t:'-~
38. 1030 1.03 1. 86 1.15 0.83

39. 475 0.79 1. 55 0.97 0.71
40. 479 0.75 1. 55 0.97 0.70
41. 480 0.82 1. 53 1. 21 0.97
42. 495 0.85 1.60 1.02 0.76
43. 494(C6D6) 1.00 1.52 0.82 0.67
44. 1032 1. 06 1.80 1.04 0.80
45. 1031 0.75 1. 55 1. 21 0.83
46. 1027 0.81 1.63 1. 20 0.82
47. 1028 0.83 1. 55 1. 24 0.84
48. 1029 0.82 1. 56 1.19 0.81
49. 962 0.84 1.29 1.10 0.74
50. 507 0.86 1.64( CC14) 1.00 0.74
51. 1034a 0.86 COOH (4.55,4.31) 0.79
52. 509 1.04 (4.12) 1.36 1. 02
53. 509a 1.05 4.5 1. 34 1.02
54. 509b 0.97 (4.49) 1.06 0.75
Table 14. I H-NMR Chemical Shifts 509
TABLE 14. (contd.).
Compound
No. H-17 H-18 H-19 H-20
55. 846 0.85 (4.23,3.67) (3.85,3.98) 0.78
56. 1033a 0.86 COOH (4.59,4.32) 0.80
57. 1034 0.88 COOH (4.22 ) 0.76
58. 1034a 0.86 COOH (4.55) 0.79
59. 1034b 0.86 COOMe (4.60) 0.81
60. 967 CHO 1. 60 1. 07 1. 00
61. 551b 0.82 1. 22 1.02 0.67
62. 1061 COOR (4.15,4.09) 0.94
63. 543 0.84 1. 57 1. 01 0.77
64. 563 0.82 COOR (4.28,3.89) 0.58
65. 562 1. 03 COOR (5.31,3.9) 0.86
66. 559 1.06 COOR (5.33,3.92) 0.92
67. 561 0.99 COOR (3.92,4.01) 0.64
68. 562 1. 04 COOR (3.91,5.30) 0.87
69. 969 COOR (4.09,4.05) 0.69
70. 970 COOR (4.00,4.10) 0.87
71. 525 COOR (4.15,4.18) 1.10
72. 526 COOR (4.29,4.27) 1.13
73. 526a COOR (4.13,4.45) 1.16
74. 900 0.89 COOMe (4.36,4.60) 0.84
75. 902 0.89 COOHe (4.62,4.54) 0.89
76. 903 0.89 COOHe (4.62,4.37) 0.85
77. 904 0.86 COOHe CHO 0.60
78. 500 0.92 1. 59 1.17 0.97
79. 500a 0.96 0.72
80. 500b 1.00 1. 59 1. 25 0.98
81. 500c 1. 27 1. 01
82. 500d 0.89 0.95 0.71
83. 960 0.81 2.02 0.92 0.85
TABLE 14. (contd.).
Compound
No. H-17 H-18 H-19 H-20
5p,10p-cis
84. 1057 0.74 (4.23,4.11) 1.12 0.76
85. 578(CC14) 0.83 1. 72 1.06 0.84
86. 580( ") 0.82 (4.54) 1.20 0.80
87. 1056a(C6D6)0.70 1.16 0.76
88. 1055a 0.79 (4.58) 1.12 0.80
89. 579(CC14) 0.80 (4.24) 1.12 0.78
90. 1058 0.76 1.70 (3.36,3.23) 0.77
91. 582(CC14) 0.83 (4.82) 1.28 0.80
92. 582a( ") 0.87 (4.70) 1.15 0.83
93. 581 0.85 (4.22) 1.35 0.80
94. 581a 0.87 1.85 1.21 0.82
95. 585 0.80 COOR 1.20 0.69
96. 584 0.85 COOR 1.26 0.77
97. 577 0.77 COOR 1.24 0.79

98. Cistodioic 0.71 COOR 1. 20 0.75
Acid
99. Cistodiol- 0.73 1.07 0.75
Acetate
1 See Figure 48 for conformations of compounds 1025a and 1035b.

2 See Figure 1 for structures of non-derivative compounds.
3 See Figure 60 for derivative compounds and naturally occurring

compounds not included in Figure 1.
TABLE 15. l3C NMR Chemical Shifts of Methyl Carbons, C-17, C-19, and C-
20, of Sa, lOa- and 5a,IO~-clerodanes.
Structure C-17 C-19 C-20 Reference

I. 5a,10a-cis-C1erodanes
1. [545]1 15.4Q 24.18 28.34 483
2. [262] 15.17 21.55 24.24 483

3. [260] 15.75 26.64 27.46 483
Table 15. I3C NMR Chemical Shifts 511
TABLE 15. (contd.).
Structure C-17 C-19 C-20 Referr.nce

4. (988) 15.75 26.53 27.46 ill
5. 15.75 26.53 28.05 483
6. 15.81 26.47 28.05 ill
7. 15.58 25.24 28.58 483
8. 15.52 25.24 28.34 483
9. 15.28 22.37 28.87 483
10. 15.28 24.54 28.11 483
11. 15.05 21.90 28.69 483
12. 15.46 24.13 28.58 483
13. 14.29 21. 73 29.28 483
14. 15.23 28.46 26.66 483
15. (1083) 15.5 31. 0 17.6 180
16. (1084) 15.7 64.8 17.2 180
17. (1085) 18.3 77 .0 22.7 180
18. (1086) 17.7 101.1 22.3 180
19. (1087) 16.7 97.8 21.8 180
20. (1088) 16.4 101. 3 21. 4 180
21. (1089) 17.0 102.6 22.2 180
22. (1090) 17.0 104.1 23.6 180
23. (1091) 16.8 176.5 21. 0 180
II. 5a,10~-trans-C1erodanes
24. (961) 15.8 19.5 17.8 483

25. 15.5 * 17.6 483
26. 15.6 * 17.6 483
27. 15.5 * 17.3 483
28. 15.3 * 17.3 483
29. 15.4 * 17.8 483
30. (1033) 15.9 65.5 18.6 464
31. [1033 Ac) 15.6 71.8 18.1 464
32. [1034 Ac) 15.6 70.1 17.8 464
33. [1034Me,Ac]15.6 70.1 17.8 464
512 6. Diterpene Analysis with Emphasis on C1erodanes
TABLE 15. (contd.).
Structure C-17 C-19 C-20 Reference

34. [1070 Me] 19.9 60.6 15.5 468
35. [1070Me,Ac]19.9 62.4 15.6 468
36. [1093Me ,Ac]18. 9 62.2 15.9 468
37. 15.3 68.1 17.2 341
38. 12.0 72.6 19.0 341
39. 11. 9 72.7 19.1 341
40. 14.4 64.2 16.3 ill

41. 15.6 70.2 17.2 341
42. 15.4 69.1 16.4 341

43. 15.3 68.1 17.6 341
44. *73.4 18.8 341

1 See Figure 61 for structures of these compounds.
TABLE 16. 1H-NMR Chemical Shifts for the Sandaracopimaranes (Structures 1-

12, Figure 62) Isolated from Garuleum and Osteosperum (156).
[4a-Me] [4,8-Me] [IO-Me] [13-Me]

H-19 H-18 H-20 H-17 H-15 H-16(c) H-16(t)
1.* 0.85 0.85 1. 00 1.22 5.73 4.77 4.82
2.* 0.83 0.85 0.95 1.01 5.64 4.76 4.79
3. 0.97 1. 23 1. 31 1.23 5.74 4.83 4.87
4.* 0.96 0.98 1.16 1.27 5.65 4.74 4.79
5. 0.87 0.87 1.18 1.26 5.73 4.81 4.86
6. 0.85 0.88 1. 00 1.31 5.67 4.90 4.92
7(1) 0.88 0.88 1. 20 1.28 5.75 5.00 5.02
(2)*0.87 0.87 1.16 1.22 5.77 4.93 4.94
8. 0.89 0.89 1. 20 1. 34 5.67 4.93 4.94
9. 0.86 0.88 1.11 1.27 5.83 4.96 4.97
10. 0.86 0.88 1.02 1.26 5.72 5.04 5.05
11. 0.96 1.25 1. 65 1.40 5.70 4.82 4.84
12. 0.89 0.91 1.42 1. 42 5.78 5.13 5.01
* solvent: CC1 4
Figure 33. Chemical Interconversion of Solidagonic Acid 513
A·
158 Solidagenone
500 Solidagonic Acid
B·
UAl H
500
5000 R - H
SOOb R - Ac
CH 2 0Ac
Pyridine Jones Reagent

5000 - - _ _ _ o_ _
500b
(~)O
500c
CH 2 0H
KOH
500c
Hydrazine hydrate
475 Kolavenol
FIGURE 33. Chemical interconversion of solidagonic acid (500) to a compound of

established absolute stereochemistry, kolavenol (475) (364, 365).
Ul
oj::>.
-
?'
S?
~
R .g
o ~
\\,\\ >
].
f!).
en
~
CH;S02C
s:
C02 H CH;S02C
~
511 511a R - C02CH;s 511e
i
f!).
en
511 b R = COCH;s o
::3
, n
OH
C0 2CH;s en
J
\\\\\
CH;S02C
o o
511f
3B-Hydroxy-5a-androstan-17-one 511c
6. £. 300 +3·26 ] 16.£ 301 -2·49 ] ~t. 2N-;soe +2·18
[
T = 34m}' ;dioxane L 1" = 36m}-l; dioxane L 1" = 38m}4; dioxane ]
,
'Tl
, OQ'
s::
@
w
~
n
[
[
o ~
511d i.
o
o
o
....,
-'""'
,
~ £.302 -2,91 '-"'
:I:
Lr = 37m}A
J ~
(S.
Er:
(S.
FIGURE 34. Chemical degradation of (-)-hardwickiic acid (511) to products permitting the assignment of ring-fusion configuration
(391). >
(")
s.:
VI
......
VI
ORIGINAL. REVlSED
OR
258 Elon~atol1d. C (R - ""~)

(Sol1do~olocton. 11)
545 Elon~atol1d. A (R - H)
(Sol1do~olocton. IV)
5411 Elon~otond. B (R - Ac)
259 Sol1dagolacton. III (R - n~)
w"'
~/~
H~O
'''''~~
H~ro
Y '__ 0'
/'...~
:' I 1'1111
~'n)
1= ;I
I I
o o
2112 Sonda~olacton. V
FIGURE 35. Original trans-ent-clerodane structures assigned as the e1ongatolide series

from Solidago elongata (18) and the solidagolactone series from S. altissima (413) and
the revised 5a,lOa-cis-normal-clerodane structures (401, 402).
Figure 35. Original trans-ent-Clerodane Structures 517
H~O
m
I
11111
----r
[-11'1 I
OR
553 Elone;otond. 0 (R - Ac)
(Solldoe;olocton. VI)
H~~O
L (' Y -'""~
h,/~)
/
lu m
~O
0'\ : 1
OR
260 ElonQatolld. E (R - Ane;) 260 Sol1doQolocton. V11
988 SolldoQolocton. VIII (R - TIe;)
ORIGINAL
REVISED
j No revision
543 So:idagolactone

239-
2390 507
B·
1075 (revised)
FIGURE 36. Attempts to correlate the structure of solidagoic acid A (239) with those of
known cis-c1erodanes: A. comparison of the methyl 1 H-NMR chemical shifts (0) of a
solidagoic acid A derivative, 239a, to those of a (-)-hardwickiic acid derivative, 507; B.
enone derivative (239b) of solidagoic acid A and the revised structure of plathyterpenone
used for comparison of CD optical properties.
Figure 38. Relative Stereochemistry of the cis-ent-Clerodane 519
262 Solldagolactone V 947 Trlcyclo8olldagolactone

FIGURE 37. Tricyclosolidagolactone (947) and possible precursor, solidagolactone V
(262).
FIGURE 38. Relative stereochemistry of the cis-ent-clerodane, 583, as determined from

X-ray analysis.
576 Haplopappic Acid
578 576b Cistodioic Acid
H H
o o o
Positive Cotton Positive Cotton Effect

578b Effect (0 +65) 576c (a +64)
o o o
Weak Cotton Weak Cotton Effect

C0 2 H Effect (a -46) (0 -33)
239 Derivative 239 Derivative
FIGURE 39. Comparison of the optical data obtained from 51J,101J-cis-ent-clerodane
derivatives of 576 and 578 to that obtained from derivatives of 5a,lOa-cis-normal
clerodane 239 (237).
Figure 40. Originally Proposed trans-nonnal-clerodane Structures 521
A· Originally Proposed Structures
o
Bedfordia Koanophyllon Centipeda
\\\
\\
0
C02 H 245 C02H 249

236 4(18)db
250 1(2)db 248 1(2)db
237 3(4)db
B· Originally Proposed Nidorella Structures
CH 20H 254
FIGURE 40. Originally proposed trans-nonnal-clerodane structures for compounds
isolated from Bedfordia, Koanophyllon, Centipeda and Nidorella.
1· 1-Poly althic acid 2· Secore seda acid (1)
3· Secore seda acid (2)

was first
FIGURE 41. Proposed structures for the 5, lO-seco-clerdanes: (1.) conyzic acid
of A'-polya lthic acid (411); (2.) first proposed structure of
assigned the structure
to strictic acid
secoreseda acid (61) with C-9 orientivity opposite to that first assigned
(3.) second propose d structure of secoreseda acid (72) and by extensio n to strictic
(420);
(573) and conyzic acids.
Figure 42. Effect of Ring Junction 523
A·
1H-NMR
CHEMICAL SHIFT:
(24·1) CH3
1·
18 0·692
=
H
19 0·792
(12·0) CH3
2·
18 0·692
19 0·925
CH 3
3· 18 0·992
19 0·767
H
CH3
4·
18 0·992
19 0·900
Gi)
B·
85
15·7 28·2
2.4 6.4
22·2 22·8
46·2 41·8
= 27·4 24·5
H
29·4 H 28·1
trans-Methyldecalln cis-Methyldecalin
FIGURE 42. The effect of ring junction configuration on the I H- and 13C-NMR chemical
shifts of methyls attached at the ring junction in parallel instances: A. androstane steroid
skeletal types 1-4; B. cis- and trans-methyldecalin.
C-1·
CH3
0·86
CH3 (axial)
0·74
H
0·92
(equatorial)
H ...~
C-2'
~ CH31 . 17
CH3
\lo'
1·64
1·06
0·83
C-3·
CH3 (axial)
0·84
FIGURE 43. I H-NMR chemical shifts (0, CDCl3) of the methyls associated with three
constitutionally equivalent representatives of the different clerodane ring-junction types,
5a-1O~-trans-ent-clerodane (C-l), 5a,lOa-cis-normal-clerodane (C-2) and 5~, lO~-cis
ent-clerodane (C-3).
Figure 44. Effect of C-6 Substitution 525
18 R
I H- NMR Chemical Shift (6, CDCl3)
Structure H-17 H-18 H-19 H-20

1. R = H 0.92 1. 64 1.17 1. 08
2. R = OH 0.86 1. 68 1. 21 1. 05
3. R OAng 0.86 1. 56 1. 28 1. 08
4. R = =0 0.87 1. 54 1. 24 1. 24
FIGURE 44. The effect of C-6 substitution on the methyl 1 H-NMR chemical shifts of
5a,lOa-cis-normal-c1erodanes (Structures 1 from 15; Structures 2,3 and 4 from 402).
,. R - H2 3· R - H2
~R-O ~R-O
B· H
FIGURE 45. Conformational variation attributed to the 5a-lOa-ciS'-normal-clerodanes: A. two

favored conformational possibilities (15); B. probable conformation of compounds containing a
18, 19-oxido linkage; C. the effect of the shielding zone of the C-2 ketone on the 1H-NMR chemical
shift of the C-9 methyl (H-20) of cis-clerodanes.
Figure 46. Two Conformations 527
c· o
o
263a
H
o
-
H
268 R - Ang
269 R - TIg
/ I
CH 3
Conformation I Conformation "

FIGURE 46. Two conformations assignable to 5a,lOa-cis-normal-clerodanes based on
the nature of the Rl and R2 substituents.
A· H
o o
2440 1066
B·
1· 2·
4·
1·64
1·64
1·94 1·95
FIGURE 47. The effect of 18, 19-oxido linkage on the probability of either conformation I
or II: A. comparison of the methyl lH-NMR chemical shifts (0, CDCI 3) of 244a and
1066; B. comparison of the methyl chemical shifts of tetrahydrofuryl-bearing cis-
clerodanes (Structures 1,3, and 5) and the corresponding furyl compounds (Structures 2,
4, and 6).
Figure 48. Methyl 1H-NMR Chemical Shifts 529
• 0
A· Conformations at -50 C
0·84
. O~y~H'
o=<~~~~
~CH., HO CH.,
1025a Conformation I (C-613-acetate: axial)
HO CH.,
N ' ,'
0·73 (' ~
o CH~
CH.,
1·04
~ . . H
H
OAe
CH.,
1 ·18
1025b Conformation II (C-6J3-acetate: equatorial)
8· Room-Temperature Chemical Shifts:
H-17 0·93
H-19 1·32
H-20 0·93
FIGURE 48. Methyl 1H-NMR chemical shifts (5, CDCI3) for the two conformations
(1025a and l025b) of 1025 observed at -50·C (170).
~~~~
CH313 \l 0 7 19
20
18
1· 582 Hydrogenolysis product 2· 545 Reduction product
Eu(pdm) 3 Addition-Induced Shift

Methyl Proton 1- 2.
H-18 10.0 3.9
H-19 9.6 5.3
H-17 1.7 2.0
H-20 4.2 3.3
FIGURE 49. Comparison of the Eu(pdmh addition-induced 1 H-NMR chemical shift

results for representative compounds of 5a-lOa-cis-normal- and 5{3,1O{3-cis-ent-
clerodanes (386, 378).
Figure 50. Transformation of Solidagolactone IV 531
NBS/THf
OH
545
-
5450
p- Toluenesulfonlc
acid
545b III
o
Br
FIGURE 50. The transformation of solidagolactone IV (545) to a product with a C-3-C-6
ether function (545b) as partial proof of a cis-ring junction (378).
t
!
22X + 57X
'T.I
ciQ.
$::=
@
VI
280a
en
c· o 2
n
8....
(1)
CI
~
DlBAL/THF §.
::s
OR ~.
0
::s
OR 0
....,
1· 280 (R - Ang), 988 (R - ng) 3· R - Ang, R - ng
~
::s
(Jq
2· SoIldagolactone (545) .. SoIIdagolactone IV epoxlde ~
i2.
epoxlclatlon product (R - H) reduotlon product (R - H) s:
(1)
'"
5-R- co-{ }-.
FIGURE 51. Structure determination ofelongatolides D (553) and E (260): A. correct structures of 553 and 260 (18, 413,
401); B. incorrect assignment of structure to the products, 260b and 260c, of the epoxidation of elongatolide E (260) furyl
derivative (402); C. correlation of the major product of the epoxidation of 545 (Figure 35B.) (Structure 2, R = H) with VI
v.>
related butenolide-containing compounds, 260, 988 and the p-bromobenzoate (Structure 5) (401). v.>
Major ,,0
\\\
[0<] -22
D
(Major:Minor:3: 1)
perbenzoic
Minor
acid
239 H
d(2)
B·
Major
[ex] -27,2
D
OH
(1·7:1·0)
p-bromo- Minor
benzoic acid
OH
545 H
d(5·1) [01.] -17·1
D
OH
FIGURE 52. The effects of C-6 substitution on the products of 3,4-epoxidation of 5a-
lOa-cis-normal clerodanes: A. epoxidation of 239 (386); B. epoxidation of 545 (401); C.
epoxidation of a 258 and 259 mixture (291); D. epoxidation of 546 (413).
Figure 53. Transformation of Solidagonic Acid 535
o
c·
o H
d(4)
m-chloro-per-
benzoic acid
OR Ulnor
?
258 (R - Ang) or 259 (R - ng)
D·
o
o
-
OAe
OAe
546
- 3·45
H
m(W1/2 =- 6)
239 Solidagoic Acid A
derivative
FIGURE 53. Transformation of solidagoic acid (239) epoxy-derivative to the 3ti-hydroxy
product (386).
C6
2L J :3
5
-
10 H2
I
<po_datlo,
0<. - EPOXIDE ~ - EPOXIDE
cou;Eling Constants
Tori equation
calculation: J3,2a = 4.88Hz (12° ) J3,2a = 0.50Hz (47.8°)
J3,2~ = 0.49Hz (108° ) J3,2~ = 2.30Hz (71.8 0 )
Observed: J3,2a = 5.1Hz J3,2a = O.OHz

J3,2~ = O.OHz J3,2~ = 1.5Hz
FIGURE 54. The application of Tori equation calculations to the prediction of H-3
coupling constants of 5a-lOa-cis-normal-c1erodane 3,4-a- and (3-epoxides (378).
Figure 55. Effect of Different C-7 Substituents 537
509 R - H 509b
509a R - Ac
COtH R
500
500a R - CH20Ac
500b R - C02CH3
1H- NMR Chemical Shift (6, CDCl3)

Structure H-19 H-20
509 1. 36 1. 02
509a 1. 34 1. 02
500 1.17 0.97
509b 1.06 0.75
SODa 0.95 0.71
500b 0.96 0.72
FIGURE 55. The effect of different C-7 substituents on the H-19 and H-20 IH-NMR
chemical shifts (0) of 50!,lOfj-trans-ent-c1erodanes.
III III
OH OH
19CH3 : OH
20 CH3
1·25
0-98
H-7 W'/2 - 9Hz H-7 W' /2 - 23Hz

FIGURE 56. The effects of C-7 a- and /3-hydroxylation on the 1 H-NMR properties of
5a,1O/3-trans-ent-clerodanes (412).
Figure 58. Conformation Assigned by McCrindle 539
Compound C19 Substitution H-20 Chern· Shift
900 CH 2 0Ac 0·84
902 CH 2 0Ang 0·89
903 CH 2 Oi-Val 0·85
1033 CH 2 0H 0·79
904 CHO 0·60

FIGURE 57. The effect of different 5a, lO{3-trans-ent-clerodane C-19 substituents on the
I H-NMR chemical shift (Il) of H-20.
H
, .~ ...~
---\
CH',,~ ~O
.~ CH
.:I
, " \
OH
FIGURE 58. Conformation assigned by McCrindle et al. (386) to the 5{3-1O{3-cis-ent-

clerodanes.
16
15
Rl
R2
18
IH-NMR Chemical Shift(CDCl3)
Structure H-17 H-18 H-19 H-20

1. R1 = c02H, R2 = CH20H 0.74 1.12 0.76
2. R1 = c02H, R2 CH20Ac 0.74 1.11 0.69
3. R1 R2 = CH20H 0.75 1.12 0.76
4. R1 = c02CH3' R2 = CH20H 0.74 1.12 0.76
5. R1 = CH2oH, R2 = c02CH3 0.75 1. 22 0.77
FIGURE 59. 1 H-NMR chemical shifts (0, CDCI 3) ofthe methyl protons on cistodioic acid
(R 1 = R2 = C02H) derivatives (33, 469).
Figure 60. Structures of Clerodane Diterpenes 541
231b 231c
o
231a X - H,H 262a
231d X - 0
",.0
HO'\\
Ok OH
26Ga 26Gb
FIGURE60. Structures of clerodane diterpenes (included in Table 14 compilation of I H-
NMR data) that are derivatives of the natural products listed in Table 2.
o
o
OR OR
260e R - H 263<1 R - AnCJ or TlCJ
260d R - Ac
COaH
1091a
2440
R R
500a R - COaCHJ 500b R - CHaOH

500d R - CHaOAc SOOe R - COaH
C~ORa
C~RJ
50ga
10lla R, • RJ • H. Rz • k
10l4a R, • Ok. Rz • k. RJ • H
10l4b R, • OH. Rz • k. RJ • CHJ
50gb 551b
521a
R
1055a R. ~
ClSTODIOL DlACETATE R. CHaOAc
10580 R. H
ClSTODIOIC ACID R· COaH
RI
581a RI • CHs•Ita • H
582a RI • CHaOAc. Ra • ~
R OR
1· (545) R ... OH 3· (260) R - Ang
2· (262) R - -0 4· (988) R - Tig
10 R-OAc 8· R - H
OH
9· R - H 12·
OR
5· R - Ang 13·
6· R ... Tig
7· R - H
FIGURE 61. Structures of clerodane diterpenes included in the compilation of 13C-NMR
data (Table 15).
14· R = Tig 15· (1083)
R,
16· (1084) R, ... R2 - CH 20H 17· (1085)
23· (1091) R, - CH3 • R2 - COO-a-L-Arab
....
-;.\\ OH
R
OI\H
18· (1086) 19· (1087) R = OH

21· (1089) R - H
HO'" -:
HO lO~OH
H
o
22· (1090) 20· (1088)
C0 2H
o
24· (961) 26· Teumaseilin, R, - R2 .. H

27· 6,19 - Oiacetylteumassilin
R, ... R2 ... Ac
\ OR2
OR,
25· Oeacetylajugarin-II 29· Ajugarin-IV
R, - R2 - H
28· Ajugarin-I, R, .. R2 = Ac
FIGURE 6l. (contd.).
30· (1033) R, - R2 - RJ - H 34· R ... H

3;· R, ... R2 - H, RJ ... Ae 35· R ... Ae
32· R, .. OAe, R2 - H, RJ - Ae
14
F
-0
O
2-Uebut-0
O:! \- OAe
OAe
o
38· 13(14)d·b· 40·
39·
~ /
~O
o
41· 42·
43· 44·
R,
11· R, = OH, R2 =H
2· R, = Ae, R2 = R3 = R4 = H
3· [277] R, = R3 = R4 = H, R2 = OH
4· [278] R, = R3 = R4 = H. R2 = OAe
5· [279] R, = R2 = R4 = H, R3 = OH
6· [284] R, = R2 = R3 = H, R4 = OAe
7· R, = R2 = H, R3 = R4 = OH
8· [292] R, = R2 = H. R3 = OH, R4 = OAe
9· [289] R, = R2 = H, R3 = OAe, R4 = OH
10· R, = R2 = R3 = H, R4 = OH
FIGURE 62. Proposed conformation and twelve representative structures of the sandara-
copimaranes isolated from Garuleum and Osteospermum (156). 1 H-NMR data for
these structures are included in Table 16.
CHAPTER 7
References
1. Achilladelis, B., and 1.R. Hanson: Studies in terpenoid biosynthesis. 1. The

biosynthesis of metabolites of Tricothecium roseum. Phytochem. 7, 589
(1968).
2. Ahmed, A.A., D.A. Gage, 1.S. Calderon, and T.J. Mabry: Labdanediterpenes
from Brickellia vernicosa. Phytochem. 25, 1385 (1986).
3. Alieva, S.A., Z.M. Putieva, E.S. Kondratenko, and N.K. Abubakirov: A
diterpene glycoside-doronicoside D-from Doronicum macrophyllum.
Khim. Prir. Soedin. 658 (1977).
4. Almqvist, S.-O., C.R. Enzell, and F.W. Wehrli: Carbon-13 NMR studies of
labdane diterpenoids. Acta Chern. Scand B 29, 695 (1975).
5. Alvarez, L., R. Mata, G. Delgado, and A. Romo de Vivar: Sesquiterpene
lactones from Viguiera hypargyrea. Phytochem. 24, 2973 (1985).
6. Amaro, T .M., and M. Adrien R.: Diterpenoides del Oxylobus glanduliferus
(Sch.-Bip.) Gray. Rev. Latinoamer. Quim. 13: 110 (1982).
7. Anderson, A.B., R. McCrindle, and E. Nakamura: Diterpenoids of Solidago
arguta Ait. The stereochemistry of cis-c1erodanes. J. Chern. Soc. Chern.
Commun. 1974, 453.
8. Angeles, E., K. Folting, P.A. Grieco, I.C. Huffman, R. Miranda, and M.
Salmon: Isolation and structure of stephalic acid, a new c1erodane diterpene
from Stevia polycephala. Phytochem. 21, 1804 (1982).
9. Anthonsen, T.: A note on the constitution of the diterpene C2oH2s03 from
Solidago canadensis L. Acta Chern. Scand. 20, 904 (1966).
10. Anthonsen, T., and G. Bergland: The diterpenoids of Solidago missouriensis
Nutt. Acta Chern. Scand. 24, 1860 (1970).
II. Anthonsen, T., and G. Bergland: The diterpenoids of some Solidago species.
Acta Chern. Scand. 25, 1924 (1971).
12. Anthonsen, T., and G. Bergland: Constitution and stereochemistry of diterpe-
noids from Solidago missouriensis Nutt. Acta Chern. Scand. 27, 1073 (1973).
13. Anthonsen, T., and S. Chantharasakul: Isolation of ent-16-kauren-19-oic acid
and ent-16-kauren-19-ol from Abrotanella nivigena Mue1!. Acta Chern.
Scand. 25, 1925 (1971).
14. Anthonsen, T., M.S. Henderson, A. Martin, R. McCrindle, and R.D.H.
Murray: Furan-containing diterpenoids from Solidago serotina Ait. Acta
Chern. Scand. 22, 351 (1968).
15. Anthonsen, T., M.S. Henderson, A. Martin, R.D.H. Murray, R. McCrindle,
and D. McMaster: Constituents of Solidago species. Part IV. Solidagoic acids
552 7. References
A and B, diterpenoids from Solidago gigantea var. serotina. Can J. Chem. 51,
1332 (1973).
16. Anthonsen, T., P.H. McCabe, R. McCrindle, and R.D.H. Murray: The
constitution and stereochemistry of solidagenone. Acta Chem. Scand. 21,2289
(1967).
17. Anthonsen, T., P.H. McCabe, R. McCrindle, and R.D.H. Murray: Constitu-
ents of Solidago species I. The constitution and stereochemistry of diterpe-
noids from Solidago canadensis L. Tetrahedron 25, 2233 (1969).
18. Anthonsen, T., and R. McCrindle: The constitution of diterpenoids from
Solidago elongata Nutt. Acta Chem. Scand. 23, 1068 (1969).
19. Apsimon, J.W., W.G. Craig, P.V. DeMarco, D.W. Mathieson, and W.B.
Whalley: The n.m.r. spectra of some diterpenes. Chem. Comm. 1966, 361.
20. Apsimon, J.W., W.G. Craig, P.V. DeMarco, D.W. Mathieson, and W.B.
Whalley: The chemical shift-III. The NMR spectra of some diterpenes.
Tetrahedron 23, 2375 (1967).
21. Arnone, A., R. Mondelli, and J. St. PyreL 13C NMR Spectroscopy of natural
substances. IV. 13C NMR Studies of trachy lobane diterpenes: complete carbon
assignment. Org. Magn. Reson. 12, 429 (1979).
22. Arriaga-Giner, F.J., E. Wollenweber, I. Schober, P. Dostal, and S. Braun: 2{3-
Hautriwaic acid, a c1erodane type diterpenoid and other terpenoids from three
Baccharis species. Phytochem. 25, 719 (1986).
23. Bahsas, A., and J. Triana: Inulaefol, nuevo furanoditerpeno del Eupatorium
inulaefolium HBK. VI. Simposium Internacional Quimica de Productos
Naturales, Monterrey, N. L., Mexico. April 23-28. 1979, 15.
24. Bailey, J.A., G.G. Vincent, and R.S. Burden: Diterpenes from Nicotiana
glutinosa and their effect on fungal growth. J. of General Microbiology. 85, 57
(1974).
25. Banerjee, S., M. Grenz, 1. Jakupovic, and F. Bohlmann: Some alicyclic
terpenoids from the tribe Anthemideae. Planta Med. 1985, 177 (1985).
26. Banerjee, S. and J. Jakupovic: Further diterpenes from Palafoxia rosea. Rev.
Latinoamer. Quim. 17,202 (1986).
27. Banerjee, S., J. Jakupovic, and R.M. King: Weitere derivate des (3-jonons aus
Haplopappus fremontii. Pharmazie 41, 157 (1986).
28. Barua, R.N., R.P. Sharma, G. Thyagarajan, W. Herz, and S.V. Govindan:
New melampolides and darutigenol from Sigesbeckia orientalis. Phytochem.
19, 323 (1980).
29. Baruah. R.N., C. Zdero, F. Bohlmann, R.M. King, and H. Robinson: Some
sesqui- and diterpenes from the tribe Eupatorieae. Phytochem. 24, 2641
(1985).
30. Bastard, 1., D. Khac Duc, M. Fetizon, M.1. Francis, P.K. Grant, R.T.
Weavers, C. Kaneko, G. Vernon Baddeley, J.-M. Bernaussau, I.R. Burfitt,
P.M. Wovkulich, and E. Wenkert: CMR spectroscopy of labdanic diterpenes
and related substances. 1. Nat. Prod. 47, 592 (1984).
31. Beale, M.H., J.R. Bearder, 1. Macmillan, A. Matsuo, and B.O. Phinney:
Diterpene acids from Helianthus species and their microbiological conversion
by Gibberellafugikuroi, Mutant BI-41a. Phytochem. 22, 875 (1983).
32. Bennett, R.D., E.R. Lieber, and E. Heftmann: Biosynthesis of steviol from (-)-
kaurene. Phytochem. 6, 1107 (1967).
33. Berti, G., O. Livi, and D. Segnini: Cistodiol and Cistodioic acid, diterpenoids
with a cis-fused c1erodane skeleton. Tetrahedron Letters 1970, 1401.
References 553
34. Bhat, S.V., P.S. Kalyanaraman, H. Kohl, and N.J. De Souza: Inuroyleanol and
7-ketoroyleanone, two novel diterpenoids of Inula royleana DC. Tetrahedron
31, 1001 (1975).
35. Bittner, M., and W.H. Watson: Phytochemical study of Haplopappus
ciliatus. Rev. Latinoamer. Quim. 13,24 (1982).
36. Bittner, M.L., V. Zabel, W.B. Smith, and W.H. Watson: A new dihydro-
trans-clerodane diacid from Haplopappus ciliatus. Phytochem. 17, 1797
(1978).
37. Bjeldanes, L.F., and T .A. Geissman: Constituents of Helianthus cilaris.
Phytochem. 11, 327 (1972).
38. Bohlmann, F.: Neues iiber die chemie der Compositen. Naturwissenschaften
67, 588 (1980).
39. Bohlmann, F., and W.-R. Abraham: Neue diterpene und weitere inhaltsstoffe aus
Helichrysum calliconum und Helichrysum heterolasium. Phytochem. 18, 889
(1979).
40. Bohlmann, F., and W.-R. Abraham: Neue diterpene aus Helichrysum
acutatum. Phytochem. 18, 1754 (1979).
41. Bohlmann, F. and W.-R. Abraham: Sesquiterpene und acetylenverbindungen
aus Cineraria-arten. Phytochem. 17, 1629 (1978).
42. Bohlmann, F., W.-R. Abraham, R.M. King, and H. Robinson: Diterpenes
from Koanophyllon species. Phytochem. 20, 1903 (1981).
43. Bohlmann, F., W.-R. Abraham, H. Robinson, and R.M. King: A new labdane
derivative and geranylphloroglucinols from Achyrocline alata. Phytochem.
19, 2475 (1980).
44. Bohlmann, F., W.-R. Abraham, H. Robinson, and R.M. King: Heliangolides
and other constituents from Bejaranoa semistriata. Phytochem. 20, 1639
(1981).
45. Bohlmann, F., W.-R. Abraham, and W.S. Sheldrick: Weitere diterpene mit
helifulvan-geriist und andere inhaltsstoffe aus Helichrysum chionosphaerum.
Phytochem. 19, 896 (1980).
46. Bohlmann, F., A. Adler, J. Jakupovic, R.M. King, and H. Robinson: A
dimeric germacranolide and other sesquiterpene lactones from Mikania
species. Phytochem. 21, 1349 (1982).
47. Bohlmann, F., A. Adler, R.M. King, and H. Robinson. ent-Labdanes from
Mikania alvimii. Phytochem. 21, 173 (1982).
48. Bohlmann, F., A. Adler, A. Schuster, R.K. Gupta, R.M. King, and H.
Robinson: Diterpenes from Mikania species. Phytochem. 20, 1899 (1981).
49. Bohlmann, F., M. Ahmed, N. Borthakur, M. Wallmeyer, J. Jakupovic, R.M.
King, and H. Robinson: Diterpenes related to grindelic acid and further
constituents from Grindelia species. Phytochem. 21, 167 (1982).
50. Bohlmann, F., M. Ahmed, 1. Jakupovic, R.M. King, and H. Robinson:
Labdane and dehydronerolidol derivatives from Brickellia dijjusa. Phyto-
chern. 21, 691 (1982).
51. Bohlmann, F., M. Ahmed, 1. Jakupovic, R.M. King, and H. Robinson:
Dimeric sesquiterpene lactones and kolavane derivatives from Gochnatia
paniculata. Phytochem. 22, 191 (1983).
52. Bohlmann, F., M. Ahmed, J. Jakupovic, R.M. King, and H. Robinson: Three
kolavane derivatives and 2iJ-angeloyloxy himachanolide from Acritopappus
longijolius. Rev. Latinoamer. Quim. 15, 16 (1984).
53. Bohlmann, F., M. Ahmed, R.M. King, and H. Robinson: Labdane and
554 7. References
eudesmane derivatives from Ageratum fastigiatum. Phytochem. 20, 1434

(1981).
54. Bohlmann, F., M. Ahmed, H. Robinson, and R.M. King: A kolavane
derivative from Liatris seariosa. Phytochem. 20, 1439 (1981).
55. Bohlmann, F., N. Ates, and J. Jakupovic: Hirsutinolides from South African
Vernonia species. Phytochem. 22,1159 (1983).
56. Bohlmann, F., N. Ates, R.M. King, and H. Robinson: Two sesquiterpenes
from Senecio species. Phytochem. 22, 1675 (1983).
57. Bohlmann, F., S. Banerjee, J. Jakupovic, M. Grenz, L.N. Misra, G. Schmeda-
Hirschmann, R.M. King, and H. Robinson: Clerodane and labdane diterpe-
noids from Baeeharis species. Phytochem. 24, 511 (1985).
58. Bohlmann, F., S. Banerjee, C. Wolfrum, J. Jakupovic, R.M. King, and H.
Robinson: Sesquiterpene lactones, geranylnerol and tremetone derivatives
from Ageratina species. Phytochem. 24, 1319 (1985).
59. Bohlmann, F., M. Bapuji, J. Jakupovic, R.M. King, and H. Robinson:
Unusual diterpenes from Briekellia eupatoriedes. Phytochem. 21, 181 (1982).
60. Bohlmann, F., M. Bapuji, R.M. King, and H. Robinson: Kolavenol derivatives
from Goyazianthus tetrastiehus. Phytochem. 21, 939 (1982).
61. Bohlmann, F., R.N. Baruah, R.M. King, and H. Robinson: Alicyclic
diterpenes from Cronquistianthus bishopii. Planta Med. 1985 167 (1985).
62. Bohlmann, F., N. Borthakur, R.M. King, and H. Robinson: Dihydroden-
droidinic acid from Pleuroeoronis pluriseta. Phytochem. 20, 2433 (1981).
63. Bohlmann, F., T. Burkhardt, and C. Zdero: Naturally Occurring Acetylenes.
Academic Press. London and New York. 1973.
64. Bohlmann, F., V. Castro, and J. Jakupovic: Germacra-l(10),4-dien-eis-6,12-
olides and elemanolides from Montanoa atriplieijolia. Phytochem. 22, 1223
(1983).
65. Bohlmann, F., T. Chau-Thi, P. Singh, and 1. Jakupovic: Alicyclic diterpenes
from Solidago species. Planta Med. 1985, 487 (1985).
66. Bohlmann, F., and H. Czerson: Neue labdan- und pimaren- derivate aus
Palafoxia rosea. Phytochem. 18, 115 (1979).
67. Bohlmann, F., A.K. Dhar, J. Jakupovic, R.M. King, and H. Robinson: Two
sesquiterpene lactones with an additional propiolactone ring from Disynaphia
halimijolia. Phytochem. 20, 1077 (1981).
68. Bohlmann, F., K. Dhar, J. Jakupovic, R.M. King, and H. Robinson: A
caryophylene derivative from Fleischmannia pycnocephaloides. Phytochem.
20, 1425 (1981).
69. Bohlmann, F., L.N. Dutta, W. Dorner, R.M. King, and H. Robinson: Zwei
neue guajanolide sowie weitere longipinenester aus Stevia-arten. Phytochem.
18, 673 (1979).
70. Bohlmann, F., L. Dutta, H. Robinson, and R.M. King: Neue labdan-derivate
aus Chrysothamnus nauseusus. Phytochem. 18, 1889 (1979).
71. Bohlmann, F., D. Ehlers, and C. Zdero: Einige neue furanoeremophilane aus
Senecio arten. Phytochem. 17,467 (1978).
72. Bohlmann, F., and U. Fritz: Neue diterpene und acetylenverbindungen aus
Nidorella-arten. Phytochem. 17, 1769 (1978).
73. Bohlmann, F., U. Fritz, H. Robinson, and R.M. King: Sesquiterpene and
diterpene derivatives from Solidago species. Phytochem. 19, 2655 (1980).
74. Bohlmann, F., U. Fritz, H. Robinson, and R.M. King: Isosesquicaren aus
References 555
Haplopappus tenuisectus. Phytochem. 18, 1749 (1979).

75. Bohlmann, F., T. Gerke, J. Jakupovic, N. Borthakur, R.M. King, and H.
Robinson: Diterpene lactones and other constituents from Wedelia and Aspilia
76. Bohlmann, F., and M. Grenz: Notiz iiber die isolierung von hautriwa-saure aus
Conyza ivaefolium Less. Chern. Ber. 105,3123 (1972).
77. Bohlmann, F., and M. Grenz: Constituents from representatives of the
Eupatorium group. Chern. Ber. 110, 1321 (1977).
78. Bohlmann, F., and M. Grenz: Atisiren-derivate aus Garuleum sonchifolium
(DC.)T. Nor!' Chern. Ber. 111, 1509 (1978).
79. Bohlmann, F., and M. Grenz: Diterpene vom sandarocopimaren-typ aus
Chrysanthemoides-arten. Phytochem. 18, 683 (1979).
80. Bohlmann, F., M. Grenz, A.K. Dhar, and M. Goodman: Labdane derivatives
and flavones from Gutierrezia dracunculoides. Phytochem. 20, 105 (1981).
81. Bohlmann, F., M. Grenz, J. Jakupovic, R.M. King, and H. Robinson: New
labdane derivatives and other consituents from Fleischmannia viscidipes.
Rev. Latinoamer. Quim. 15, 1 (1984).
82. Bohlmann, F., M. Grenz, and H. Schwarz: Neue diterpene aus Hinterhubera
imbricata Cuatr. Chern. Ber. 106, 2579 (1973).
83. Bohlmann, F., M. Grenz, P. Wegner, andJ. Jakupovic: Clerodan-derivateund
neuartige diterpene aus Conyza scabrida DC. Liebigs Ann. Chern. 1983,
2008.
84. Bohlmann, F., R.K. Gupta, R.M. King, and H. Robinson: A clerodane lactone
and a tremetone derivative from Bahianthus viscidus. Phytochem. 20, 331
(1981).
85. Bohlmann, F., R.K. Gupta, H. Robinson, and R.M. King: Labdane derivatives
and a himachalanolide from Acritopappus longifolius. Phytochem. 20, 275
(1981).
86. Bohlmann, F., L. Hartono, and 1. Jakupovic: A diterpene related to
erythroxydiol from Helichrysum refluxum. Phytochem. 24, 611 (1985).
87. Bohlmann, F., L. Hartono, C. Zdero, and J. Jakupovic: Constituents of the
genus Oxylobus. Phytochem. 24, 1111 (1985).
88. Bohlmann, F., and H. Hoffmann: Further amides from Echinecea purpurea.
Phytochem. 22, 1173 (1983).
89. Bohlmann, F., and J. Jakupovic: Uber neue chromene und andere inhaltsstoffe
von Lagascea rigida. Phytochem. 17, 1677 (1978).
90. Bohlmann, F., and J. Jakupovic: Neue labdan-derivate und andere inhaltsstoffe
aus Relhania acerosa. Phytochem. 18, 631 (1979).
91. Bohlmann, F., and J. Jakupovic: Neue labdan-derivate und sesquiterpene aus
Silphium-arten. Phytochem. 18, 1987 (1979).
92. Bohlmann, F., 1. Jakupovic, M. Ahmed, M. Grenz, H. Suding, H. Robinson,
and R.M. King: Germacranolides and diterpenes from Viguiera species.
Phytochem. 20, 113 (1981).
93. Bohlmann, F., J. Jakupovic, M. Ahmed, M. Wallmeyer, H. Robinson, and
R.M. King: Labdane derivatives from Hemizonia species. Phytochem. 20,
2383 (1981).
94. Bohlmann, F., 1. Jakupovic, N. Ates, A. Schuster, J. Pickardt, R.M. King,
and H. Robinson: Steiractinolide, eine neue gruppe von sesquiterpenlactonen.
Liebigs Ann. Chern. 1983,962 (1983).
556 7. References
95. Bohlmann, F., J. Jakupovic, A.K. Dhar, R.M. King, and H. Robinson:
Heliangolides and diterpenes from Hartwrightia floridana. Phytochem. 20,
843 (1981).
96. Bohlmann, F., J. Jakupovic, A.K. Dhar, R.M. King, and H. Robinson: Two
sesquiterpene and three diterpene lactones from Acanthospermum australe.
Phytochem. 20, 1081 (1981).
97. Bohlmann, F., J. Jakupovic, M. Hashemi-Nejad, and S. Huneck: Clerodane
diterpenoids from Aster alpinus. Phytochem. 24, 608 (1985).
98. Bohlmann, F., J. Jakupovic, R.M. King, and H. Robinson: Neue ent-atisiren-
und ent-kaurensiiure-derivate aus Helianthus-arten. Phytochem. 19, 863
(1980).
99. Bohlmann, F., J. Jakupovic, R.M. King, and H. Robinson: New germacrano-
lides, guaianolides and rearranged guaianolides from Lasiolaena santosii.
Phytochem. 20, 1613 (1981).
100. Bohlmann, F., J. Jakupovic, R.M. King, and H. Robinson: New labdane
derivatives from Madia sativa. Phytochem. 21, 1103 (1982).
101. Bohlmann, F., J. Jakupovic, H. Robinson, and R.M. King: Neue diterpene aus
Schkuhria-arten. Phytochem. 19, 881 (1980).
102. Bohlmann, F., J. Jakupovic, H. Robinson, and R.M. King: Diterpenes and
other constituents of Morithamnus crassus. Phytochem. 19, 2769 (1980).
103. Bohlmann, F., J. Jakupovic, and A. Schuster: Germacranolides from Peryme-
nium klattianum and Perymeniopsis ovalifolia. Phytochem. 24,495 (1985).
104. Bohlmann, F., J. Jakupovic, and A. Schuster: 8-Hydroxypegolettiolide, a
sesquiterpene lactone with a new carbon skeleton and further constituents from
Pegolettia senegalensis. Phytochem. 22, 1637 (1983).
105. Bohlmann, F., J. Jakupovic, A. Schuster, R.M. King and H. Robinson:
Germacranolide, hydroxyverbenon und ent-kaur-15(16)-en-17, 19-disiiure aus
Helianthus occidentalis var. dowellianus. Planta Med. 1984, 202 (1984).
106. Bohlmann, F., J. Jakupovic, A. Schuster, R.M. King, and H. Robinson:
Guaianolides and homoditerpenes from Lasiolena morii. Phytochem. 21, 161
(1982).
107. Bohlmann, F., J. Jakupovic, A. Schuster, R.M. King, and H. Robinson: New
me1ampolides, kaurene derivatives and other constituents from !chthyothere
species. Phytochem. 21,2317 (1982).
108. Bohlmann, F., J. Jakupovic, A. Schuster, R.M. King, and H. Robinson:
Homogeranylnerol derivatives and a melampolide from Smallanthus glabra-
tus. Phytochem. 24, 1309 (1985).
109. Bohlmann, F., J. Jakupovic, C. Zdero, R.M. King, and H. Robinson: Neue
melampolide und cis,cis-germacranolide aus vertretern der subtribus Melam-
podiinae. Phytochem. 18, 625 (1979).
110. Bohlmann, F., W. Knauf, M. Grenz, and M.A. Lane: Ein neues diterpen aus
Xanthocephalum linearifolium. Phytochem. 18, 2040 (1979).
111. Bohlmann, F., W. Knauf, R.M. King, and H. Robinson: Ein neues diterpen
und weitere inhaltsstoffe aus Baccharis-arten. Phytochem. 18, 1011 (1979).
112. Bohlamnn, F., and K.-H. Knoll: Neue pimardien-derivate aus Othonna-arten.
Phytochem. 15, 1072 (1976).
113. Bohlmann, F., K.-H. Knoll, R.M. King, and H. Robinson: Neue a-santalen-
und 1abdan-derivate aus Ayapana amygdalina. Phytochem. 18, 1997 (1979).
114. Bohlmann, F., K.-H. Knoll, H. Robinson, and R.M. King: Neue kauren-
References 557
derivate und melampolide aus Smallanthus uvedalia. Phytochem. 19, 107

(1980).
115. Bohlmann, F., K.-H. Knoll, H. Robinson, and R.M. King: Neue eudesmano-
lide aus Steiractinia mollis. Phytochem. 19, 971 (1980).
116. Bohlmann, F., W. Kramp, M. Grenz, H. Robinson, and R.M. King:
Diterpenes from Baccharis species. Phytochem. 20, 1907 (1981).
117. Bohlmann, F., W. Kramp, 1. Jakupovic, H. Robinson, and R.M. King:
Diterpenes from Baccharis species. Phytochem. 21, 399 (1982).
118. Bohlmann, F., and N. Le Van: Uber neue diterpene aus Dimorphotheca
pluvialis Moench. Chern. Ber. 109, 1446 (1976).
119. Bohlmann, F., and N. Le Van: Sesquiterpenlactone und polyine aus der gattung
Arctotis. Phytochem. 16,487 (1977).
120. Bohlmann, F., and N. Le Van: Neuen kaurensiiure-derivate aus Wedelia-arten.
Phytochem. 16, 579 (1977).
121. Bohlmann, F., and N. Le Van: Neue guajanolide aus Podachaenium eminens.
Phytochem. 16, 1304 (1977).
122. Bohlmann, F., and N. Le Van: Neue sesqui- und diterpene aus BedJordia
salicin a . Phytochem. 17, 1173 (1978).
123. Bohlmann, F. and N. Le Van: Neue kaurensiiure-derivate und germacranolide aus
Montanoa pteropoda. Phytochem. 17, 1957 (1978).
124. Bohlmann, F., and M. Lonitz: Neue sadaracopimardien-derivate, sesquiter-
pene und sesquiterpenlactone aus Zexmenia-arten. Chern. Ber. 111, 843
(1978).
125. Bohlmann, F., and M. Lonitz: Uber die inhaltsstoffe von Zexmenia gnapha-
loides und die synthese von valerenan-derivaten. Chern. Ber. 113, 2410
(1980).
126. Bohlmann, F., G.-W. Ludwig, J. Jakupovic, R.M. King, and H. Robinson: A
daucanolide and further farnesene derivatives from Ageratum Jastigiatum.
Phytochem. 22, 983 (1983).
127. Bohlmann, F., and P.K. Mahanta: Kaurenic acid derivatives from Adenos-
temma caJJrum. Phytochem. 17, 814, (1978).
128. Bohlmann, F., and P.K. Mahanta: Ein neue diterpensiiure aus Centipeda
orbicularis. Phytochem. 18, 1067 (1979).
129. Bohlmann, F., L.N. Misra, and 1. Jakupovic: Pseudoguaianolides and
carabrone derivatives from Loxothysanus sinuatus. Phytochem. 24, 1021
(1985).
130. Bohlmann, F., L.N. Misra, 1. Jakupovic, R.M. King, and H. Robinson:
Guaianolides, heliangolides, diterpenes and cycloartenol derivatives from
Balsamorhiza sagittata. Phytochem. 24, 2029 (1985).
131. Bohlmann, F., A.A. Natu, and P .K. Mahanta: Neue diterpene und germa-
cranolide aus Mikania-arten. Phytochem. 17,483 (1978).
132. Bohlmann, F., and N. Rao: Neue hydroxyacetophenon-derivate aus Espeletia
schultzii. Chern. Ber. 106, 3035 (1973).
133. Bohlmann, F., H. Robinson, and R.M. King: Chemotaxonomy of the genus
Plagiocheilus. Phytochem. 19, 2235 (1980).
134. Bohlmann, F., E. Rosenberg, R.M. King, and H. Robinson: Neue labdan-
derivate aus Aristeguietia buddleaeJolia. Phytochem. 19, 977 (1980).
135. Bohlmann, F., C. Scheidges, R.M. King, and H. Robinson: Five labdane
derivatives from Koanophyllon conglobatum. Phytochem. 23, 1190 (1984).
558 7. References
136. Bohlmann, F., C. Scheidges, C. Zdero, R.M. King, and H. Robinson: Ent-
labdanes from Baccharis sternbergiana. Phytochem. 23, 1109 (1984).
137. Bohlmann, F., G. Schmeda-Hirschmann, and J. Jakupovic: He1iangolides and
germacranolides from Disynaphia multicrenulata. Phytochem. 23, 1435
(1984).
138. Bohlmann, F., G. Schmeda-Hirschmann, and 1. Jakupovic: Neue melampolide
aus Acanthosperum australe. Planta Med. 1984, 37 (1984).
139. Bohlmann, F., G. Schmeda-Hirschmann, and 1. Jakupovic: Nor-ent-labdan
derivate aus Austroeupatorium inulaefolium. Planta Med. 1984, 199 (1984).
140. Bohlmann, F., P. Singh, and J. Jakupovic: Further ineupatorolide-1ike
germacranolides from Inula cuspidata. Phytochem. 21, 157 (1982).
141. Bohlmann, F., P. Singh, J. Jakupovic, R.M. King, and H. Robinson:
Eudesmanolides from Dimerostemma brasilianum. Phytochem. 21, 1343
(1982).
142. Bohlmann, F., P. Singh, 1. Jakupovic, H. Robinson, and R.M. King: An
epoxygermacranolide and further consitituents from Mikania species. Phyto-
chern. 21, 705 (1982).
143. Bohlmann, F., P. Singh, R.K. Singh, K.C. Joshi, and J. Jakupovic: A
diterpene with a new carbon skeleton from Solidago altissima. Phytochem.
24, 1114 (1985).
144. Bohlmann, F., H. Suding, J. Cuatrecasas, R.M. King, and H. Robinson: Neue
diterpene aus der subtribus Espeletiinae. Phytochem. 19, 267 (1980).
145. Bohlmann, F., H. Suding, J. Cuatrecasas, H. Robinson, and R.M. King:
Tricyclic sesquiterpenes and further diterpenes from Espeletiopsis species.
Phytochem. 19, 2399 (1980).
146. Bohlmann, F., A. Suwita, R.M. King, and H. Robinson: Neue ent-labdan-
derivate aus Austroeupatorium chaparense. Phytochem. 19, 111 (1980).
147. Bohlmann, F., A. Suwita, and T.J. Mabry: New 1abdane derivatives and
further constituents of Brickellia species. Phytochem. 17,763 (1978).
148. Bohlmann, F., A. Suwita, H. Robinson, and R.M. King: Six guaianolides from
Stylotrichium rotundifolium. Phytochem. 20, 1887 (1981).
149. Bohlmann, F., K. Umemoto, and J. Jakupovic: Pseudoguaianolides related to
confertin from Stevia isomeca. Phytochem. 24, 1017 (1985).
150. Bohlmann, F., M. Wallmeyer, and J. Jakupovic: A new seco-1abdane
derivative from Athrixia elata. Phytochrem. 21, 1806 (1982).
151. Bohlmann, F., M. Wallmeyer, 1. Jakupovic, and 1. Ziesche: Diterpenes and
sesquiterpenes from Osteospermum species, Phytochem. 22, 1645 (1983).
152. Bohlmann, F., M. Wallmeyer, R.M. King, and H. Robinson: 2-0xo-labda-
8(17), 13-dien-15-ol from Ophryosporus chilca. Phytochem. 23, 1513 (1984).
153. Bohlmann, F., and P. Wegner: Ent-beyer-15-ene derivatives from Nidorella
anomala. Phytochem. 21, 1175 (1982).
154. Bohlmann, F., and P. Wegner: Three diterpenes from Conyza podocephala.
Phytochem. 21, 1693 (1982).
155. Bohlmann, F., P. Wegner, and J. Jakupovic: Unusual diterpenes and
sesquitepene xy10sides from Nidorella hottentotica. Phytochem. 21, 1109
(1982).
156. Bohlmann, F., G. Weickgenannt, and C. Zdero: Neue diterpene aus der tribus
Calendulaceae (sic.). Chern. Ber. 106, 826 (1973).
References 559
157. Bohlmann, F., and C. Zdero: Notiz tiber ein weiteres diterpen aus Osteospermum
subulatum DC. Chern. Ber. 108, 362 (1975).
158. Bohlmann, F., and C. Zdero: Uber inhaltsstoffe der gattung Brickellia. Chern.
Ber. 109, 1436 (1976).
159. Bohlmann, F., and C. Zdero: Uber ein neues diterpen aus Melampodium
perfoliatum (Carv.)A. Gray. Chern. Ber. 109, 1670 (1976).
160. Bohlmann, F., and C. Zdero: Neue terpen-inhaltsstoffe aus Verbesina-arten.
Phytochem. 15, 1310 (1976).
161. Bohlmann, F., and C. Zdero: Inhaltsstoffe der gattung Polymnia. Phytochem.
16, 492 (1977).
162. Bohlmann, F., and C. Zdero: Ein neue diterpensiiure aus Perymenium
ecuadoricum. Phytochem. 16, 786 (1977).
163. Bohlmann, F., and C. Zdero: Ein neues clerodan-derivat sowie weitere
inhaltsstoffe aus der gattung Macowania. Phytochem. 16, 1583 (1977).
164. Bohlmann, F., and C. Zdero: Neue norkauren- und thymol derivate aus
Athrixia-arten. Phytochem. 16, 1773 (1977).
165. Bohlmann, F., and C. Zdero: Diterpenes with a new carbon skeleton from
Printzia laxa. Phytochem. 17,487 (1978).
166. Bohlmann, F., and C. Zdero: Ein neues kaurensiiure und ein euparin-derivat
aus Oyedaea-arten. Phytochem. 18, 492 (1979).
167. Bohlmann, F., and C. Zdero: Neue phloroglucin-derivate aus Helichrysum
natalitium und Helichrysum bellum. Phytochem. 18. 641 (1979).
168. Bohlmann, F., and C. Zdero: Korrektur der konstitutionen von diterpenen aus
Palafoxia rosea. Phytochem. 18, 2038 (1979).
169. Bohlmann, F., and C. Zdero: Sandaracopimarene derivatives from Senecio
subrubriflorus. Phytochem. 21, 1697 (1982).
170. Bohlmann, F. and C. Zdero: Stevisalicinon, ein neuer Diterpentyp, sowie
weitere inhaltsstoffe aus Stevia-arten. Liebigs Ann. Chern. 1764 (1985).
171. Bohlmann, F., C. Zdero, W.-R. Abraham, A. Suwita, and M. Grenz: Neue
diterpene und neue dihydrochalkon-derivate sowie weitere inhaltsstoffe aus
Helichrysum-arten. Phytochem. 19, 873 (1980).
172. Bohlmann, F., C. Zdero, and M. Ahmed: New sesquiterpene lactones,
geranyllinalol derivatives and other constituents from Geigeria species.
Phytochem. 21, 1679 (1982).
173. Bohlmann, F., C. Zdero, D. Berger, A. Suwita, P. Mahanta, and C. Jeffrey:
Neue furanoeremophilane und weitere inhaltsstoffe aus stidafrikanischen
Senecio-arten. Phytochem. 18, 79 (1979).
174. Bohlmann, F., C. Zdero, J. Cuatrecasas, R.M. King, and H. Robinson: Neue
sesquiterpene und norditerpene aus vertretern der gattung Libanothamnus.
Phytochem. 19, 1145 (1980).
175. Bohlmann, F., C. Zdero, L. Fiedler, H. Robinson, and R.M. King: A labdane
derivative from Chromolaena collina and a p-hydroxyacetophenone deriva-
tive from Stomatanthes corumbensis. Phytochem. 20, 1141 (1981).
176. Bohlmann, F., C. Zdero, and M. Grenz: New sesquiterpenes of the genus
Othonna. Chern. Ber. 107, 3928 (1974).
177. Bohlmann, F., C. Zdero, and M. Grenz: Weitere inhaltsstoffe aus vertretern
der Eupatorium-gruppe. Chern. Ber. 110, 1034 (1977).
178. Bohlmann, F., C. Zdero, M. Grenz, A.K. Dhar, H. Robinson, and R.M. King:
560 7. References
Five diterpenes and other constituents from nine Baccharis species. Phyto-
chern. 20, 281 (1981).
179. Bohlmann, F., C. Zdero, R.K. Gupta, R.M. King, and H. Robinson:
Diterpenes and teranorditerpenes from Acritopappus species. Phytochem. 19,
2695 (1980).
180. Bohlmann, F., C. Zdero, E. Hoffmann, P.K. Mahanta, and W. Dorner: Neue
diterpene und sesquiterpene aus siidafrikanischen Helichrysum-arten. Phyto-
chern. 17, 1917 (1978).
181. Bohlmann, F., C. Zdero, and S. Huneck: Diterpenes from Heteropappus
altaicus. Phytochem. 24, 1027 (1985).
182. Bohlmann, F., C. Zdero, J. Jakupovic, N. Ates, R.M. King, and H. Robinson:
Steiractinolide aus Aspi/ia und Wedelia-arten. Liebigs Ann. Chern. 1983,
1257 (1983).
183. Bohlmann, F., C. Zdero, J. Jakupovic, T. Gerke, M. Wallmeyer, R.M. King,
and H. Robinson: Neue sesquiterpenlactone und rosan-derivate aus Trichogo-
nia-arten. Liebigs Ann. Chern. 1984, 162.
184. Bohlmann, F., C. Zdero, 1. Jakupovic, R.M. King, and H. Robinson:
Diterpenes from Acritopappus confertus. Phytochem. 22, 2243 (1983).
185. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Neue labdan-derivate
aus Carterothamnus anomalochaeta. Phytochem. 18, 621 (1979).
186. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Ein neues labdan-
derivat und neue thymol-derivate aus Bishovia boliviensis. Phytochem. 18,
1234 (1979).
187. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Neue labdan-derivate
aus Gutierrezia-arten. Phytochem. 18, 1533 (1979).
188. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Ein neues germacran-
8,12-olid und neue diterpene aus Polymnia canadensis. Phytochem. 19, 115
(1980).
189. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Germacranolides, a
guaianolide with a ~-Iactone ring and further constituents from Grazielia
190. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Thirteen kolavane
derivatives from Symphyopappus species. Phytochem. 20, 1657 (1981).
191. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Sesquiterpenes,
guaianolides and diterpenes from Stevia myriadenia. Phytochem. 21, 2021
(1982).
192. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: New germacranolides
and other constituents from Trichogoniopsis morii. Phytochem. 21, 2035
(1982).
193. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Eudesmanolides and
kaurane derivatives from Wedelia hookeriana. Phytochem. 21, 2329 (1982).
194. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: New labdan-derivate
aus Aristeguietia pseudoarborea. Liebigs Ann. Chern. 1983, 2127.
195. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Epoxycannabinolid
und diterpene mit neuem kohlenstoffgeriist aus Villanova titicaensis. Liebigs
Ann. Chern. 1984,250.
196. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Kingidiol, a kolavane
derivative from Baccharis kingii. Phytochem. 23, 1511 (1984).
197. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Gutierrezial and
References 561
further diterpenes from Gutierrezia sarothrae. Phytochem. 23, 2007 (1984).

198. Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: A further geranylnerol
derivative from Helianthopsis species. Phytochem. 24, 1108 (1985).
199. Bohlmann, F., C. Zdero, and P. Mahanta: Neue diterpene aus Dimorpho-
theca- und Viguiera-arten. Phytochem. 16, 1073 (1977).
200. Bohlmann, F., C. Zdero, H. Robinson, and R.M. King: Ein neues germacren-
derivat sowie ein diterpenmalonat aus Baccharis arten. Phytochem. 18, 1993
(1979).
201. Bohlmann, F., C. Zdero, H. Robinson, and R.M. King: 15a-Methylacryl-
oyloxy-ent-kaurenic acid from Ichthyothere species. Phytochem. 20, 522
(1981).
202. Bohlmann, F., C. Zdero, H. Robinson, and R.M. King: A diterpene, a
sesquiterpene quinone and flavanones from Wyethia helenioides. Phytochem. 20,
2245 (1981).
203. Bohlmann, F., C. Zdero, H. Robinson, and R.M. King: Labdane derivatives from
Planaltoa lychnophoroides. Phytochem. 21, 465 (1982).
204. Bohlmann, F., C. Zdero, H. Robinson, and R.M. King: germacranolides from
Lychnophora species. Phytochem. 21, 1087 (1982).
205. Bohlmann, F., C. Zdero, G. Schmeda-Hirschmann, J. Jakupovic, V. Castro, R.M.
King, and H. Robinson: Heliangolide, trachyloban und villanovan-derivate aus
Viguiera-arten. Liebigs. Ann. Chern. 1984, 495 (1984).
206. Bohlmann, F., C. Zdero, and S. Schoneweiss: tiber die Inhaltsstoffe aus Stevia-
arten. Chern. Ber 109, 3366 (1976).
207. Bohlmann, F., C. Zdero, and B. L. Turner: Guaianolides and heliangolides from
Hymenopappus newberryi. Phytochem. 23, 1055 (1984).
208. Bohlmann, F., C. Zdero, R. Zeisberg, and W.S. Sheldrick: Helifulvanolsaure -ein
neues diterpen mit anomalem kohlenstoffgerust aus Helichrysum fulvum. Phyto-
chern. 18, 1359 (1979).
209. Bohlmann, F., and J. Ziesche: Neue germacren-derivate aus Senecio-arten.
Phytochem. 18, 1489 (1979).
210. Bohlmann, F., and J. Ziesche: Neue diterpene aus Gnaphalium-arten. Phytochem.
19, 71 (1980).
211. Bohlmann, F., J. Ziesche, R.M. King, and H. Robinson: Neuemelampolide aus
Smallanthus fruticosus. Phytochem. 19, 973 (1980).
212. Bohlmann, F., 1. Ziesche, R.M. King, and H. Robinson: Seven furanoere-
mophilanes from three Senecio species. Phytochem. 19, 2675 (1980).
213. Bohlmann, F., J. Ziesche, R.M. King, and H. Robinson: Eudesmanolides and
diterpenes from Wedelia trilobata and an ent-kaurenic acid derivative from
Aspilia parvifolia. Phytochem. 20, 751 (1981).
214. Bohlmann, F., J. Ziesche, R.M. King, and H. Robinson: Eudesmanolides and
other constituents from Dimerostemma asperatum. Phytochem. 20, 1335 (1981).
215. Bohlmann, F., J. Ziesche, R.M. King, and H. Robinson: Eudesmanolides,
guaianolides, germacranolides and elemanolides from Zinnia species. Phytochem.
20, 1623 (1981).
216. Bohlmann, F., J. Ziesche, R.M. King, and H. Robinson: A pseudoguaianolide and a
hydroxygeranylnerol from Kingianthus paradoxus. Phytochem. 20, 1146 (1981).
217. Bohlmann, F., P. Zitzkowski, A. Suwita, and L. Fiedler: cis-Kolaveninsiiure
und weitere inhaltsstoffe aus vertretern der tribus Eupatorieae. Phytochem. 17,
2101 (1978).
562 7. References
218. Brieskorn, C.H., and E. Pohlmann: Diterpene vom kaurantyp aus der composite
Espeietia schultzii (Wedd.). Tetrahedron Lett., 566 (1968).
219. Brieskorn, C.H., and E. Pohlmann: Kaurandien-(9(1l).16)-saure-(19) und 15a-
acetoxy-kauren-(16)-saure-(19). Chern. Ber. 102, 2621 (1969).
220. Brunn, T., L.M. Jackman, and E. Stenhagen: Grindelic and oxygrindelic acids.
Acta. Chern. Scand. 16, 1675 (1962).
221. Calderon, J .S., and J .R. Puig: Diterpenos tipo labdano de Stevia origanoides.
X. Simposium Internacional Quimica de Productos Naturales, Monterrey, N.
L., Mexico. April 28-30, 1983. p. 6.
222. Calderon, J.S., Quijano, L., Cristia, M., Gomez, F., and T. Rios: Labdane
diterpenes from Brickellia veronicaefolia. Phytochem. 22, 1783 (1983).
223. Calderon, 1.S., L. Quijano, M. Garduno, F. Gomez, and T. Rios: 2a-iso-
valeroyloxy-eperuic acid, a diterpene from Eupatorium petioiare. Phytochem. 22,
2617 (1983).
224. Canonica, L., B. Rindone, and C. Scolastico: Structure and stereochemistry of
psiadiol, a new diterpenoid. Tetrahedron Lett. 2639 (1967).
225. Canonica, L., B. Rindone, and C. Scolastico: A new diterpene with pimarane
skeleton. Tetrahedron Lett. 4801 (1969).
226. Carlquist, S.: Structure and ontogeny of glandular trichomes of Madinae
(Compositae). Amer. 1. Bot. 45, 675 (1958).
227. Castro, V. and 1. Jakupovic: Two further 6,12-cis-germacranolides from
Montanoa tomentosa subsp. xanthiifolia. Phytochem. 24, 2449 (1985).
228. Castro, V. and J. Jakupovic: 4iJ,19-Epoxy-norkaurene and other diterpenes
from Mikania banisteriae. Phytochem. 24, 2450 (1985).
229. Ceccarelli, N., R. Lorenzi, and A. Alpi: Kaurene and kaurenol biosynthesis in cell-
free systems of Phaseolus coccineus suspensor. Phytochem. 18, 1657 (1979).
230. Cheng, P.C., C. Hufford, and N.J. Doorenbos: Isolation of ll-hydroxylated
kauranic acids from Adenostemma iavenia. J. Nat. Prod. 42, 183 (1979).
231. Connolly, J.D., F. Orsini, F. Pelizzoni, and G. Ricca: 13C NMR spectra of
cassane diterpenoids. The stereochemistry of the caesalpins. Org. Magn.
Reson. 17, 163 (1981).
232. Craig, J.C., M.L. Mole, S. Billets, and F. EI-Feraly: Isolation and identifica-
tion of the hypoglycemic agent, carboxyatractylate from Xanthium struma-
rium. Phytochem. 15, 1178 (1976).
233. Cronquist, A.: The Compositae revisited. Brittonia 29, 137 (1977).
234. Croteau, R., and M.A. Johnson: Biosynthesis of terpenoids in glandular
trichomes. In: E. Rodriguez (ed.). Biology and Chemistry of Plant Trichomes.
Plenum Press (1984).
235. Cruse, W.B.T., M.N.G. James, and Ali A. AI-Shamma, J.K. Beal, and R.W.
Doskotch: The molecular structure of gutierolide, a novel chloro-diterpenoid
lactone. J. Chern. Soc. Chern. Commun. 1278 (1971).
236. Cuatrecasas, T.: Prima Flora Colombiana. 3. Compositae-Astereae. Webbia
24, 1 (1969).
237. Cuevas, L.A., F. Garcia Jimenez, and A. Romo de Vivar: Estructura de la
estenolobina. Rev. Latinoamer. Quim. 3, 22 (1972).
238. Cutler, H.G.: Carboxyatractyloside: A compound from Xanthium strumarium
and Atractylis gummifera with plant growth inhibiting properties. The probable
"Inhibitor A." J. Nat. Prod. 46, 609 (1983).
References 563
239. Danieli, B., E. Bombardelli, A. Bonati, and B. Gabetta: Structure of the

diterpenoid carboxyatractyloside. Phytochem. 11, 3501 (1972).
240. Delgado, G., L. Alvarez, and A. Romo de Vivar: Terpenoids and a flavan-3-01
from Viguiera quinqueradiata. Phytochem. 23, 675 (1984).
241. Delgado, G., L. Alvarez, and A. Romo de Vivar: 15-0xo-zoapatlin, a diterpene
lactone from Viguiera maculata. Phytochem. 23, 2674 (1984).
242. Delgado, G., H. Candenas, G. Pelaez, and A. Romo de Vivar: Terpenoids from
Viguiera excelsa and Viguiera oaxacana. J. Nat. Prod. 47, 1042 (1984).
243. Delgado, G., and A. Romo de Vivar: ent-Kaurenoid methyesters from Viguiera
stenoloba, structural revision of stenolobin and its biomimetic conversion to
zoapatlin. Chern. Lett. 1237 (1984).
244. Delgado, G., A. Romo de Vivar, J. Cardenas, R. Pereda-Miranda, and E. Huerta:
ent-Beyerene and ent-atisene-diterpenes from Viguiera insignis. Phytochem. 23,
2285 (1984).
245. Delgado, G., A. Romo de Vivar, A. Ortega, J. Cardenas, and E. O. Schlemper:
Diterpenoids from Viguiera insignis. Phytochem. 22, 1227 (1983).
246. Dell, B., and A.J. McComb: Resin production and glandular hairs in Beyeria
viscosa (Labill.) Miq. (Euphorbiaceae). Aust. J. Bot. 25, 195 (1974).
247. Dell, B., and A.J. McComb: Glandular hairs, resin production, and habitat of
Newcastelia viscida E. Pritzel (Dicrastylidaceae). Aust. J. Bot. 23, 373 (1975).
248. Dominguez, X.A.: Eupatorieae-chemical review, In V.H. Heywood, J.B.
Harborne and B.L. Turner (eds.). The biology and chemistry of the
Compositae. vol. 1, 487-502, Academic Press, London (1977).
249. Dominguez, X.A., D. Butruille, I. Sandler, and G. Vazquez: Identification de la
solidagenona en Solidago sempervirens. Rev. Latinoamer. Quim. 6, 159 (1975).
250. Dominquez, X.A., C. Cisneros, E. Guajardo, T., R. Villarreal, and A. Zamudio:
Diterpenoids from Palafoxia rosea. Phytochem. 14, 1665 (1975).
251. Dominquez, X.A., C. Cisneros, R. Guajardo, R. Villarreal, V. Zebel, and W.H.
Watson: Jesromotetrol, a new diterpene from Palafoxia rosea (Compositae). Rev.
Latinoamer. Quim. 9, 99 (1978).
252. Dominquez, X.A., and S. Jimenez Jimennez: Aislamiento y estructuras del
julslimtetrol, nor-julslimdiolona y la isocumambrina, metabolitos secundarius del
Croptilon divaricatum (Compuesta). Rev. Latinoamer. Quim. 3, 177 (1973).
253. Dominguez, X.A., J. Verde S., N.E. Guerra R., E. Ellenmaurer, and J.
Jakupovic: A nor-diterpene and other constituents from Isocoma coronopijo-
lia. Phytochem. 25,2893 (1986).
254. Edwards, O.E., G. Feniak, and M. Los: Diterpenoid quinones of Inula royleana
D.C. Can. J. Chern. 40, 1540 (1962).
255. Edwards, O.E., and M.N. Rodger: The alkaloids of Inula royleana. Can. J.
Chern. 37, 1187 (1959).
256. Eguren, L., A. Perales, J. Fayos, B. Rodriquez, G. Savona, and F. Piozzi:
New neoclerodane diterpenoid containing an oxetane ring isolated from
Teucrium chamaedrys. X-ray structure determination. 1. Org. Chern. 47,
4157 (1982).
257. EI-Emary, N.A., G. Kusano, and T. Takemoto: Kaurenoids from Cacalia
bulbifera. Phytochem. 14, 1660 (1975).
258. Elliger, C.A., D.F. Zinkel, B.G. Chan, and A.C. Waiss, Jr.: Diterpene acids as
larval growth inhibitors. Experientia 32, 1364 (1976).
564 7. References
259. EI-Naggar, S.F., R.W. Doskotch, T.M. O'Dell, and L. Girard: Antifeedant
diterpenes for the gypsy moth larvae from Kalmia lati/olia: Isolation and
characterization of ten grayanoids. J. Nat. Prod. 43, 617 (1980).
260. Evans, F.1., and CJ. Soper: The tigliane, daphnane and ingenane diterpenes, their
chemistry, distribution and biological activities. A review. Lloydia 41, 193 (1978).
261. Evans, F.1., and S.E. Taylor: Pro-inflammatory, tumour-promoting and anti-
tumour diterpenes of the plant families Euphorbiaceae and Thymelaeaceae.
Fortschritte Chern. Org. Naturst. 44, 1 (1984).
262. Fahn, A.: Secretory Tissues in Plants. Chap. 9 (158-222), Tissues secreting
lipophilic substances. Academic Press, London, New York, and San Fran-
cisco.
263. Ferguson, G., W.C. Marsh, R. McCrindle, and E. Nakamura: Stereochemistry
of clerodanes. X-ray structure of a key diterpenoid from Solidago arguta. 1.
Chern. Soc. Chern. Commun. 299 (1975).
264. Ferguson, G., R. McCrindle, S.T. Murphy, and M. Parvez: Further diterpenoid
constituents of Helianthus annuus L. Crystal and molecular structure of methyl
ent-15~-hydroxy-trachyloban-19-oate. 1. Chern. Res. 5,200 (1982).
265. Fernandez-Gadea, F., M.L. Jimeno, and B. Rodriguez: Complexation of
hydroxylated ent-kaurane diterpenoids with boric acid as an aid to the
assignment of the 13C NMR spectra. Org. Magn. Reson. 22, 515 (1984).
266. Fischer, N.H., E.J. Olivier, and H.D. Fischer: The biogenesis and chemistry
of sesquiterpene lactones, In: W. Hertz, H. Grisebach and G. W. Kirby (eds.).
Progress in the chemistry of organic natural products, 48-390. Spring-Verlag,
New York (1979).
267. Fujita, E., K. Fuji, Y. Nagao, M. Node, and M. Ochiai: Bull. Inst. Chern.
Res., Kyoto Univ., 61, 142 (1983).
268. Gage, D.A.: Chemical data and their bearing upon generic delineations in the
Eupatorieae. Taxon 34, 61 (1985).
269. Gage, D.A.: A Chemosystematic Study of the genus Piptothrix (Compositae,
Eupatorieae). Doctoral Dissertation. The University of Texas at Austin (1986).
270. Ganguly, S.N., T. Ganguly, and S.M. Sircar: Gibberellins of Enhydrafluctuans.
Phytochem. 11, 3433 (1972).
271. Gao, F., M. Leidig, and T.J. Mabry: ent-Labdane derivatives from Gutierrezia
grandis. Phytochem. 24, 1541 (1985).
272. Gao, F., M. Leidig, and T.1. Mabry: Diterpene glycosides from Gutierrezia
sphaerocephala. Phytochem. 25, 1371 (1986).
273. Gao, F., and T.1. Mabry: An acyclic diterpene from Viguiera deltoidea.
Phytochem. 24, 3061 (1985).
274. Gao, F., and T.1. Mabry: Ten cis-clerodane-type diterpene lactones from
Gutierrezia texana. Phytochem. 26, 209 (1987).
275. Gao, F., M. Miski, D.A. Gage, and TJ. Mabry: Terpenoid constituents of
Viguiera dentata. J. Nat. Prod. 48, 316 (1985).
276. Gao, F., M. Miski, D.A. Gage, J.A. Norris, and TJ. Mabry: Terpenoids from
Viguiera potosina. J. Nat. Prod. 48,489 (1985).
277. Gao, F., H. Wang, and T.J. Mabry: Sesquiterpene lactones and flavonoids
from Helianthus species. 1. Nat. Prod. 50, 23 (1987).
278. Garcia, E.E., E. Guerreiro, and P. Joseph-Nathan: ent-Pimaradiene diterpenes
from Gochnatia glutinosa. Phytochem. 24, 3059 (1985).
References 565
279. Geissman, T.A., and D.H.G. Crout: Organic Chemistry of Secondary Plant
Metabolism, Chap. 10 (Diterpenoid Compounds) pp. 291-311. Freeman,
Cooper and Company, San Francisco.
280. Gershenzon, J., and T.J. Mabry: Sesquiterpene lactones from a Texas population
of Helianthus maximiliani. Phytochem. 23, 1959 (1984).
281. Gershenzon, J., and T.J. Mabry: Furanoheliangolides from Helianthus schweinit-
zii. Phytochem. 23, 2557 (1984).
282. Gershenzon, J., T.J. Mabry, J.D. Korp, and I. Bernal: Germacranolides from
Helianthus cali/omicus. Phytochem. 23, 2561.
283. Gianello, 1. C., and o. S. Giordano: Barticulidiol, un nuevo furano diterpeno
aislado de Baccharis articulata Lam (Persoon). Rev. Lationamer. Quim. 13, 76
(1982).
284. Givovich, A., A. San-Martin, and M. Castillo: Neo-clerodane diterpenoids
from Baccharis incarum. Phytochem. 25, 2829 (1986).
285. Glasby, 1.S.: Encyclopaedia of the Terpenoids, Vois. 1 and 2. Wiley-
Interscience Publication, Chichester and New York (1982).
286. Gomez, G.F., 1.S. Calderon, L., Quijano, and T. Rios: Acido brickelico C, un
neuvo diterpeno aislado de Brickellia sp. VIII. Simposium Internacional
Quimica de Productos Naturales, Monterrey, N. L., Mexico. March 26-28,
1981.
287. Gomez, F., L. Quijano, 1.S. Calderon, and T. Rios: 3a-Angeloyloxy-2a-hydroxy-
cativic acid, a new diterpene from Brickellia paniculata. Phytochem. 22, 1292
(1983).
288. Gonzalez, A.G., J.M. Artega, B.M. Fraga, M.G. Hernandez, and J. Fayos:
The structure of jhanilactone. Experientia 34, 554 (1978).
289. Gonzalez, A.G., J.M. Artega, J.L. Breton, and B.M. Fraga: Five new labdane
diterpene oxides from Eupatorium jhanii. Phytochem. 16, 107 (1977).
290. Gonzalez, A.G., 1.1. Mendoza, 1.G. Luis, A.G. Ravelo, X.A. Dominguez,
and G. Cano: Diterpenes from Palajoxia texana. Phytochem. 24, 3056
(1985).
291. Goswami, A., R.N. Barua, R.P. Sharma, 1.N. Baruah, P. Kulanthaivel, and
W. Herz: Clerodanes from Solidago virgaurea. Phytochem. 23, 837 (1984).
292. Grau, 1.: Astereae-systematic review. In: The Biology and Chemistry of the
Compositae (Heywood, V.H., J.B. Harborne, and B.L. Turner, eds.). New
York and London: Academic Press. 1977.
293. Guerreiro, E., 1. Kavka, and O.S. Giordano: Acido I-hidroxigrindelico en
Grindelia pulchella. Rev. Latinoamer. Quim. 13, 72 (1982).
294. Guerreiro, E., J. Kavka, 1.R. Saad, M.A. Oriental, and O.S. Giordano:
Acidos diterpenicos en Grindelia pulchella and G. chiloensis Cabr. Rev.
295. Guerrero, C., and A. Romo de Vivar: Estructura y estereoquimica de la
bacchofertina; diterpeno aislado de Baccharis conjerrta H.B.K. Rev. Lati-
noamer. Quim. 4, 178 (1973).
296. Gutierrez, A.B., 1.C. Oberti, P. Kulanthaivel, and W. Herz: Sesquiterpene
lactones and diterpenes from Mikania periplocijolia. Phytochem. 24, 2967
(1985).
297. Hahn, D.W., E.W. Ericson, M.T. Lai, and A. Probst: Antifertility activity of
Montanoa tomentosa (zoapatle). Contraception 23, 133 (1981).
566 7. References
298. Hansel, R., E.-M. Cybulski, B. <;:ubuk~u, A.H. Meri~li, F. Bohlmann, and C.
Zdero: Neue pyron-derivate aus Helichrysum-arten. Phytochem. 19, 639
(1980).
299. Hanson, J .R.: The biosynthesis of the diterpenes. In: Progress in the Chemistry
of Organic Natural Products (Herz, W., H. Grisebach, and G. W. Kirby, eds.).
Wien and New York: Springer-Verlag. 1971.
300. Hanson, J.R.: The bicyclic diterpenes. In: Progress in Phytochemistry
(Reinhold, L., and Y. Liwschitz, eds.). London: Interscience Publishers of
John Wiley and Sons. 1972.
301. Hanson, J.R.: The di- and sesquiterpenes. In: Chemistry of Terpenes and
Terpenoids (Newman, A.A., ed.). London and New York: Academic Press.
1972.
302. Hanson, J.R. (ed.): Terpenoids and Steroids (Specialist Periodical Reports),
Vol. 12. London: The Royal Society of Chemistry. 1983.
303. Hanson, J.R.: The biosynthesis of C5 -C 20 terpenoid compounds. Natural
Products Reports 1, 443 (1984).
304. Hanson, J.R.: Diterpenoids. Natural Products Reports 1, 171 (1984).
307. Hanson, J.R.: Diterpenoids. Natural Products Reports 3,307 (1986).
308. Hanson, J .R.: The chemistry of the tetracyclic diterpenoids-X. Some
beyerene 2 and 3-alcohols. Tetrahedron 26,2711 (1970).
309. Hanson, J.R., G. Savona, and M. Siverns: 13C Nuclear magnetic resonance
spectra and microbiological hydroxylation of 7a- and 7J3-hydroxykaurenolide.
J.C.S. Perkin I 1974, 2002.
310. Hanson, J.R., M. Siverns, F. Piozzi, and G. Savona: The 13C Nuclear
magnetic resonance spectra of kauranoid diterpenes. J .C.S. Perkin I 1976,
114.
311. Hanson, J.R., and A.F. White: Studies in terpenoid biosynthesis II. The
biosynthesis of steviol. Phytochem. 7, 595 (1968).
312. Harborne, J.B.: Inuleae-chemical review. In: The Biology and Chemistry of
the Compositae (Heywood, V.H., J.B. Harborne and B.L. Turner, eds.). New
313. Hedden, P., and J.E. Grabbe: Kaurenolide biosynthesis in a cell-free system
from Cucurbita maxima seeds. Phytochem. 20, 1011 (1981).
314. Hegnauer, R.: Compositae. In: Chemotaxonomie der Pflanzen, Vol. 3. Basel:
Birkhauser Verlag. 1964.
315. Hegnauer, R.: The chemistry of the Compositae. In: The Biology and
Chemistry of the Compositae (Heywood, V.H., J.B. Harborne, and B.L.
Turner, eds.). New York and London: Academic Press. 1977.
316. Heiser, C.B., D.M. Smith, S.B. Clevenger, and W.C. Martin: The North
American Sunflowers (Helianthus). Bull. Torr. Bot. Club 22, 1 (1969).
317. Henderson, M.S., R. McCrindle, and D. McMaster: Constituents of Solidago
species. Part V. Non-acidic diterpenoids from Solidago gigantea var.
serotina. Can. J. Chern. 51, 1346 (1973).
318. Henderson, M.S., R.D.H. Murray, R. McCrindle, and D. McMaster:
Constituents of Solidago species. Part III. The constitution of diterpenoids
from Solidago juncea Ait. Can. J. Chern. 51, 1322 (1973).
References 567
319. Herz, W.: Astereae-chemical review. In: The Biology and Chemistry of the
Compositae (Heywood, V.H., J.B. Harborne, and B.L. Turner, eds.). New
320. Herz, W., S.V. Bhat, and R. Murari: The diterpene darutigenol from
Palafoxia arida. Phytochem. 17, 1060 (1978).
321. Herz, W., and M. Bruno: Heliangolides, kauranes and other constituents of
Helianthus heterophyllus. Phytochem. 25, 1913 (1986).
322. Herz, W., D. Gage, and N. Kumar: Damsinic acid and ambrosanolides from
vegetative Ambrosia hispida. Phytochem. 20, 1601 (1981).
323. Herz, W., S. V. Govindan, and J. F. Blount: Tetracyclic analogues of the rosane
lactones from Eupatorium album. J. Org. Chern. 44, 2999 (1979).
324. Herz, W., S.V. Govindan, and K. Watanabe: Diterpenes of Helianthus
rigidus and H. saliei/olius. Phytochem. 21, 946 (1982).
325. Herz, W., and P. Kulanthaivel: Eudesmanolides and ent-pimaranes from
Liatris laevigata. Phytochem. 22, 715 (1983).
326. Herz, W., and P. Kulanthaivel: Ent-kaurenes and trachylobanes from
Helianthus radula. Phytochem. 22, 2543 (1983).
327. Herz, W., and P. Kulanthaivel: Ent-pimaranes, ent-kauranes, heliangolides
and other constituents of three Helianthus species. Phytochem. 23, 1453
(1984).
328. Herz, W., and P. Kulanthaivel: Ent-kauranes and lOa-methyl-eudesman-
8aH, 12-o1ides from Wedelia ealyeina and Wedelia hispida. Phytochem. 23,
2271 (1984).
329. Herz, W., and P. Kulanthaivel: Trihydroxy-C I8 -acids and a labdane from
Rudbeekia fulgida. Phytochem. 24, 89 (1985).
330. Herz, W., and P. Kulanthaivel: Diterpenes and sesquiterpene lactones from
Mikania eongesta. Phytochem. 24, 1761 (1985).
331. Herz, W., and P. Kulanthaivel: Diterpenes from Viguiera porteri. J. Nat.
Prod. 48, 676 (1985).
332. Herz, W., P. Kulanthaivel, and K. Watanabe: Ent-kauranes and other
constituents of three Helianthus species. Phytochem. 22, 2021 (1983).
333. Herz, W., and N. Kumar: Sesquiterpene lactones from Helianthus grosseser-
ratus. Phytochem. 20,99 (1981).
334. Herz, W., A.-M. Pilotti, A.-C. Soderholm, LK. Shuhama, and W. Vich-
newski: New ent-clerodane-type diterpenoids from Baeeharis trimera. J. Org.
Chern. 42, 3913 (1977).
335. Herz, W., and R.P. Sharma: Ligantrol and ligantrol mono acetate , two new
linear polyoxgenated diterpenes from Liatris elegans. J. Org. Chem. 40, 192
(1975).
336. Herz, W., and R.P. Sharma: New hydroxylated ent-kauranoic acids from
Eupatorium album. J. Org. Chem. 41, 1021 (1976).
337. Herz, W., K. Watanabe, P. Kulanthaivel, and J.F. Blount: Cycloartanes from
Lindheimera texana. Phytochem. 24,2645 (1985).
338. Hochmannova, J., L. Novotny, and V. Herout: Hydrocarbons from Petasites
albus (L.)Gaertn. rhizomes. ColI. Czech. Chem. Commun. 27, 2711 (1962).
339. Hoeneisen, M. and M. Silva: Quimica y actividad biologica de algunas
Compositae chilenas. Rev. Latinoamer. Quim. 17,24 (1986).
340. Hoffmann, J.J., B.E. Kingsolver, S.P. McLaughlin, and B.N. Timmerman:
568 7. References
Production of resins by arid-adapted Astereae. In: Recent Advances in

Phytochemistry (Timmermann, B.N., C. Steelink, and F.A. Loewus, eds.),
Vol. 18, p. 251. New York and London: Plenum Press. 1984.
341. Hoffmann, J.J., S.P. McLaughlin, S.D. Jolad, K.H. Schram, M.S. Tempesta,
and R.B. Bates: Constituents of Chrysothamnus paniculatus (Compositae):
Chrysothame, a new diterpene, and 6-oxogrindelic acid. J. Org. Chern. 47,
1725 (1982).
342. Hosozawa, S., N. Kato, and K. Munakata: Antifeeding active substances for
insects in Caryopteris divaricata Maxim. Agr. BioI. Chern. 38, 823 (1974).
343. Hubert, T.D., D.F. Wiemer: Ant-repellent terpenoids from Melampodium
divaricatum. Phytochem. 24, 1197 (1985).
344. Huneck, S., Y. Asakawa, Z. Taira, A.F. Cameron, J.D. Connolly, and D.S.
Rycroft: Gymnocolin, a new cis-clerodane diterpenoid from the liverwort,
Gymnocolea in/lata. Crystal structure analysis. Tetrahedron Lett. 24, 115 (1983).
345. Hutchison, M., P. Lewer, and 1. Macmillan: Carbon-13 nuclear magnetic
resonance spectra of eighteen derivatives of ent-kaur-16-en-19-oic acid. 1.
Chern. Soc. Perkin Trans. 11984,2363.
346. Jakupovic, 1., S. Banerjee, F. Bohlmann, R.M. King, and H. Robinson: New
diterpenes from Chiliotrichium rosmarini/olium and Nardophyllum lanatum.
Tetrahedron 42, 1305 (1986).
347. Jakupovic, 1., R.N. Baruah, F. Bohlmann, R.M. King, and H. Robinson: New
alicyclic diterpenes and ent-Iabdanes from Guterrezia solbrigii. Tetrahedron
41, 4537 (1985).
348. Jakupovic, J., R.N. Baruah, C. Zdero, F. Eid, V.P. Pathak, T.V. Chau-Thi,
F. Bohlmann, R.M. King, and H. Robinson: Further diterpenes from plants of
the Compositae, subtribe Solidagininae. Phytochem. 25, 1873 (1986).
349. Jakupovic, J., E. Ellmauerer, F. Bohlmann, R.M. King, and H. Robinson:
ent-Labdanes from Austrobrickellia patens. Phytochem. 25, 1927 (1986).
350. Jakupovic, J., E. Ellmauerer, F. Bohlmann, A. Whittemore, and D.A. Gage:
Diterpenes from Eupatorium turbinatum. Phytochem. 25,2677 (1986).
351. Jakupovic, 1., J. Kuhnke, A. Schuster, M.A. Metwally and F. Bohlmann:
Phloroglucinol derivatives and other constituents from South American
Helichrysum species. Phytochem. 25, 1133 (1986).
352. Jeffries, P.R., J.R. Knox, K.R. Price, B. Scaf: Constituents of the tumor-
inhibitory extract of Olearia muelleri. Aust. 1. Chern. 27, 221 (1974).
353. Jiang, J.B., M.J. Urbanski, and Z.G. Hajos: Total synthesis of dioxane
analogues related to zoapatanol. J. Org. Chern. 48,2001 (1983).
354. Jimenez, E.M., and M. Gonzalez de la Parra: nuevo alcohol diterpenico
aislado de Piqueria trinervia Cav. Rev. Latinoamer. Quim. 14,20 (1983).
355. Kaneda, N., H. Kohda, K. Yamasaki, O. Tanaka, and K. Nishi: Paniculosides
I-V. Diterpene glucosides from Stevia ovata Lag. Chern. Pharm. Bull. 26,
2266 (1978).
356. Kanojia, R.M., M.P. Wachter, S.D. Levine, R.E. Adams, R. Chen, E. Chin,
M.L. Cotter, A.F. Hirsch, R. Huettemann, V.V. Kane, P. Ostrowski, and C.J.
Shaw: Isolation and structural elucidation of zoapatanol and montanol, novel
oxepane diterpenoids from the Mexican plant zoapatle (Montanoa tomen-
tosa). J. Org. Chern. 47, 1310 (1982).
357. Khac Manh Duc, D., M. Fetizon, S. Lazare, P.K. Grant, M.l. Nicholls,
References 569
H.T.L. Liau, M.I. Francis, J. Poisson, I.-M. Bernassau, N.F. Roque, P.M.
Wovkulich, and E. Wenkert: 13C NMR spectroscopy of tetracarbocyclic
diterpenes and related substances. Tetrahedron 37,2371 (1981).
358. Kim, J.H., K.D. Han, K. Yamasaki, and O. Tanaka: Darutoside, a diterpenoid
from Siegesbeckia pubescens and its structure revision. Phytochem. 18, 894
(1979).
359. Kinghorn, A.D., D.D. Soejarto, N.P.D. Nanayakhara, C.M. Compadre, H.C.
Makapugay, J.M. Hovanec-Brown, P.I. Medon, and S.K. Kamath: A
phytochemical screening procedure for sweet ent-kaurene glycosides in the
genus Stevia. I. Nat. Prod. 47,439 (1984).
360. Knudsen, F., W. Vilegas, F. Oliveira, and N.F. Roque: Pimaradiene
diterpenes from Mikania triangularis. Phytochem. 25, 1240 (1986).
361. Kobayashi, M., S. Horikawa, I.H. Degrandi, J. veno, and H. Mitsuhashi:
Dulcosides A and B, new diterpene glycosides from Stevia rebaudiana.
Phytochem. 16, 1405 (1977).
362. Kohda, H., R. Kasai, K. Yamasaki, K. Murakami, and O. Tanaka: New sweet
diterpene glycosides from Stevia rebaudiana. Phytochem. 15, 981 (1976).
363. Kohda, H., O. Tanaka, and K. Nishi: Diterpene-glycosides of Stevia
paniculata Lag.: Structures of aglycones. Chern. Pharm. Bull. 24, 1040
(1976).
364. Kusumoto, S., T. Okazaki, A. Ohsuka, and M. Kotake: The structure of
solidagonic acid, a bitter principle of goldenrod. Tetrahedron Lett. 40, 4325
(1968).
365. Kusumoto, S., T. Okazaki, A. Ohsuka, and M. Kotake: The structure and
stereochemistry of solidagonic acid. Bulletin of the Chemical Society of Japan.
42, 812 (1969).
366. Lassak, E.V., and J. T. Pinhey: The constituents of some Helichrysum species
(family Compositae). Aust. I. Chern. 21, 1927 (1968).
367. Lee, E.F., J. Gershenzon, and T.I. Mabry: Terpenoids of Helianthus
nuttallii. J. Nat. Prod. 47, 1021 (1984).
368. Le Quesne, P.W., G.A. Cooper-Driver, M. Villani, M.N. Do, P.A. Morrow,
and D.A. Tonkin: Biologically active diterpenes from Solidago species. Page
271 in: A. Rahman and P. W. Le Quesne (eds.). New Trends in Natural
Products Chemistry. Studies in Organic Chemistry, Vol. 26. Elsevier Scien-
tific Publishers. Amsterdam (1986).
369. Lequesne, P.W., V. Honkan, K.D. Onan, P.A. Morrow, and D. Tonkyn:
Oxidized kaurene derivatives from leaves of Solidago missouriensis and S.
rigida. Phytochem. 24, 1785 (1985).
370. Le Van, N., and T.V. Cuong Pham: Viscidic acid A and B, two ent-Iabdane
derivatives from Chrysothamnus viscidi/lorus. Phytochem. 19, 1971 (1980).
371. Levan, N., and N.J. Fischer: Three new melampolide sesquiterpenes,
poly mat in A, B, and C, from Polymnia maculata. Phytochem. 18, 851
(1979).
372. Levine, S.D., D.W. Hahn, M.L. Cotter, F.C. Greenslade, R.M. Kanojia,
S.A. Pasquale, M. Wachter, and I.L. McGuire: The Mexican plant zoapade
(Montanoa tomentosa) in reproductive medicine. Past, present and future.
Journal of Reproductive Medicine 26, 524 (1981).
373. Lloyd, H.A., S.L. Evans, and H.M. Fales: Terpene alcohols of Helichrysum
570 7. References
dendroideum. (1978).
374. Lloyd, H.A., and H.M. Fales: Terpene alcohols of Helichrysum dendroideum.
Tetrahedron Lett. 48, 4891 (1967).
375. Luteijn, I.M., A. Van Veldhuizen, and A. De Groot: The assignment of l3C
NMR shift data in clerodanes and related structures. Organic Magnetic
Resonance 19, 95 (1982).
376. Mahanto, S.B., A.K. Sen, P.C. Mazumbar, and K. Yamasaki: Diterpenes of
Conyza stricta, identification of conyzic acid, seconidoresedasaure and strictic
acid. Phytochem. 20, 850 (1981).
377. Manabe, S., N. Enoki, and C. Nishino: Application of the CD homoallylic
benzoate method as a chiroptical tool for determination of absolute configuration.
Tetrahedron Lett. 26, 2213 (1985).
378. Manabe, S. and C. Nishino: Stereochemistry of cis-clerodane diterpenes.
Tetrahedron 42, 3461 (1986).
379. Manchand, P.S., I.F. Blount, T. McCabe, and 1. Clardy: Structure of
evillosin, a novellabdane diterpenoid lactone from Eupatorium villosum Sw.
1. Org. Chern. 44, 1322 (1979).
380. Mangoni, L., and M. Belardini: Sui componenti della Grindelia robusta. Nota
II. Acido 6-oxo-grindelico. Gass. Chim. Ital. 92, 983 (1962).
381. Mangoni, L., and M. Belardini: Sui componenti della Grindelia robusta. Nota
III. Acido 7a,8a-oxido-diidrogrindelico. Gass. Chim. Ital. 92, 995 (1962).
382. Marcelle, G.B., N. Bunyapraphatsara, G.A. Cordell, H.H.S. Fong, K.C.
Nicolaou, and R.E. Zipkin: Studies on Zoapatle I. The extraction of zoapatle
(Montanoa tomentosa) and the identification of 21-normontanol as the initial
decomposition product of zoapatanol. 1. Nat. Prod. 48, 739 (1985).
383. Mathur, S.B., and C.M. Fermin: Terpenes of Mikania mongenansis.
Phytochem. 12, 226 (1973).
384. Mathur, S.B., P. Garcia Tello, C.M. Fermin, and V. Mora-Arellano:
Terpenoids of Mikania monagasensis and their biological activities. Rev.
385. McCrindle, R., and E. Nakamura: Constituents of Solidago species. Part VI.
The constitution of diterpenoids from a chemically distinct variety of Solidago
serotina. Can. 1. Chern 52,2029 (1974).
386. McCrindle, R., E. Nakamura, and A.B. Anderson: Constituents of Solidago
species. Part VII. Constitution and stereochemistry of the cis-clerodanes from
Solidago arguta Ait. and of related diterpenoids. 1. Chern. Soc. Perkin Trans.
I. 15, 1590 (1976).
387. Melek, F.R., D.A. Gage, 1. Gershenzon, and T.1. Mabry: Sesquiterpene
lactone and diterpene constituents of Helianthus annuus. Phytochem. 24,
1537 (1985).
388. Merxmiiller, H., P. Leins, and H. Roessler: Inuleae-systematic review. In:
The Biology and Chemistry of the Compositae (Heywood, V.H., 1.B.
Harborne, and B.L. Turner, eds.), Vol. 1. London: Academic Press.
389. Michie, M.J., and W.W. Reid: Biosynthesis of complex terpenes in the leaf
cuticle and trichomes of Nicotiana tabacum. Nature 218, 578 (1968).
390. Misra, L.N., J. Jakupovic, F. Bohlmann, and G. Schmeda-Hirschmann:
Isodaucane derivatives, norsesquiterpenes and clerodanes from Chromolaena
laevigata. Tetrahedron 41, 5353 (1985).
References 571
39l. Misra, R., R.C. Pandey, and Sukh Dev: The absolute stereochemistry of
hardwickiic acid and its congeners. Tetrahedron Letters 1968, 268l.
392. Mitscher, L.A., G.S.R. Rao, T. Veysoglu, S. Drake, and T. Haas: Isolation
and identification of trachyloban-19-oic and (-)-kaur-16-en-19-oic acids as
antimicrobial agents from the prairie sunflower, Helianthus annuus. J. Nat.
Prod. 46, 745 (1983).
393. Miyakado, M., N. Ohno, H. Yoshioka, T.J. Mabry, and T. Whiffin:
Gymnospermin: A new labdantriol from Gymnosperma glutinosa. Phyto-
chern. 13, 189 (1974).
394. Morales Mendez, A., A. Usubillaga, A.K. Banerjee, and T. Nakano: Studies
on the constituents of Espeletia weddellii. Planta Med. 24, 243 (1973).
395. Mossa, J.R., 1.M. Cassady, M.D. Antoun, S.R. Byrn, A.T. McKenzie, J.F.
Kozlowski, and P. Main: Saudin, a hypoglycemic diterpenoid with a novel 6,7-
secolabdane carbon skeleton from Cluytia richardiana. J. Org. Chern. 50, 916
(1985).
396. Muradian, J., M. Motidome, and P.C. Ferreira: Flavonols and (-)-kaur-16-en-
19-oic acid from Mikania hirsutissima DC. var. hirsutissima. Rev. Lati-
noamer. Quim. 8, 88 (1977).
397. Murakami, T., T. Isa, and T. Satake: Eine neuuntersuchung der inhaltsstoffe von
Siegesbeckia pubescens Makino. Tetrahedron Lett. 50,4991 (1973).
398. Nair, A.G.R., S. Subramanan, F. Bohlmann, S. Schoneweiss, and T.J. Mabry:
A new diterpene galactoside from Acanthospermum hispidum. Phytochem.
15, 1776 (1976).
399. Nakano, T., and A. Martin: Synthesis of labda-8(17), 13(14)-diene-15, 16-01ide
and 15,16-epoxy-labda-8(17),13(16)-14-triene and their rearrangement to
c1erodane derivatives. Tetrahedron 38, 1217 (1982).
400. Nicholas, H.J.: Biosynthesis and metabolism of [14C] sc1areol. Biochem.
Biophys. Acta 84, 80 (1964).
40l. Nishino, C., S. Manabe, M. Kazui, and T. Matsuzaki: Piscicidal cis-c1erodane
diterpenes from Solidago altissima L.: Absolute configurations of 5a,lOa-cis-
c1erodanes. Tetrahedron Lett. 25, 2809 (1984).
402. Niwa, M., and S. Yamamura: Stereostructures of several solidagolactones
(elongatolides). Tetrahedron Lett. 22, 2789 (1981).
403. Nurmukhamedova, M.R., N.D. Abdullaev, and G.P. Sidyakin: Diterpenoids
of Pulicaria salvii/olia. II. Structure of salvicin. Khim. Prir. Soedin. 299
(1986).
404. Nurmukhamedova, M.R., S.Z. Kasymov, N.D. Abdullaev, G.P. Sidyakin,
and M.R. Yagudaev: Diterpenoids of Pulicaria salvii/olia I. Structures of
salvin and salvinin. Khim. Prir. Soedin. 201 (1985).
405. Oberti, J.C., A.B. Pomilio, and E.G. Gros: Diterpenes and sterols from
Wedelia glauca. Phytochem. 19, 2051 (1980).
406. Oberti, J.C., V.E. Sosa, P. Kulanthaivel, and W. Herz: Ent-norlabdane triols
from Austroeupatorium inulae/olium. Phytochem. 23,2003 (1984).
407. Oehlschlager, A.C., and G. Ourisson: A comparison of in vivo and in vitro
skeletal transformations of diterpenes. In: Terpenoids in Plants (Pridham, J .B.,
ed.). London and New York: Academic Press. 1967.
408. Oelrichs, P.P., P.J. Vallely, J.K. MacLeod, and I.A.S. Lewis: Isolation of a
new potential antitumor compound from Wedelia asperrima. 1. Nat. Prod. 43,
572 7. References
414 (1980).
409. Ohno, N., J. Geshenzon, P. Newman, and T.J. Mabry: Diterpene carboxylic
acids and a heliangolide from Helianthus angustifolius. Phytochem. 20, 2393
(1981).
410. Ohno, N., and T.J. Mabry: Sesquiterpene lactones and diterpene carboxylic
acids in Helianthus niveus subspecies canescens. Phytochem. 19,609 (1980).
411. Ohno, N., T.J. Mabry, V. Zabel, and W.H. Watson: Tetrachyrin, a new
rearranged kaurenoid lactone, and diterpene acid from Tetrachryon oriza-
baensis and Helianthus debilis. Phytochem. 18, 1687 (1979).
412. Ohsuka, A., S. Kusumoto, and M. Kotake: The steric structures of diterpene
carboxylic acids from Solidago altissima L. Nippon Kagaku Kaishi 1973, 590.
413. Okazaki, T., A. Ohsuka, and M. Kotake: Structure of diterpene lactones from
Solidago altissima L. Nippon Kagaku Kaishi 1973, 584.
414. Oriental, M.A., E. Guerreiro, and O.S. Giordano: Diterpene acids from
Grindelia aegialitis. Rev. Latinoamer. Quim. 15, 73 (1984).
415. Ortega, A., R. Martinez, and c.L. Garcia: Los diterpenos de Stevia salicifolia
Cav. Estructura del stevinsol and salicifoliol. Rev. Latinoamer. Quim. 11, 45
(1980).
416. Ortega, A., F.J. Morales, and M. Salmon: Kaurenic acid derivatives from
Stevia eupatoria. Phytochem. 24, 1850 (1985).
417. Oshima, Y., G.A. Cordell, and H.H.S. Fong: Oxepane diterpenes from
Montanoa tomentosa. Phytochem. 25, 2567 (1986).
418. Oshima, Y., J. Saito, and H. Hikino: Sterebins A, B, C, and D, bisnorditerpe-
noids of Stevia rebaudiana leaves. Tetrahedron 42, 6443 (1986).
419. Oshima, Y., S.-M. Wong, C. Konno, G.A. Cordell, D.P. Waller, D.D.
Soejarto, and H.H.S. Fong: Studies on Zoapatle, II. Leucantholide, a novel
sesquiterpene lactone from Montanoa leucantha ssp. leucantha. J. Nat. Prod.
49,313 (1986).
420. Ourisson, G.: Some aspects of the distribution of diterpenes in plants. In:
Chemistry in Botanical Classification (Nobel Foundation, Stockholm), Nobel
Symposium 25. New York and London: Academic Press. 1973).
421. Pakrashi, S.c., P.P. Ghosh Dastidar, and E. Ali: Newer (-)-kaurene derivatives
from Enhydra f/uctuans Lour. Indian J. Chern. 9, 84 (1971).
422. Pakrashi, S.C., P.P. Ghosh Dastidar, and S.K. Gupta: Diterpenoids from
Enhydra fluctuans. Phytochem. 9,459 (1970).
423. Pandey, D.C., A.K. Singhal, N.C. Barua, R.P. Sharma, J.N. Baruah, K.
Watanabe, P. Kulanthaivel, and W. Herz: Stereochemistry of strictic acid and
related furanoditerpenes from Conyza japonica and Grangea maderaspa-
tana. Phytochem.23, 391 (1984).
424. Patra, A., A.K. Mitra, S. Biswas, C.D. Gupta, T.K. Chatterjee, K. Basu, and
A.K. Barua: Carbon-13 NMR spectra of some labdane diterpenoids. Org. Magn.
Reson. 17, 301 (1981).
425. Pezzuto, J.M.: Chemistry, metabolism and biological activity of steviol (ent-
13-hydroxykaur-16-en-19-oic acid), the aglycone of stevioside. Page 371 in A.
Rahman and P.W. Le Quesne (eds.). New Trends in Natural Products
Chemistry. Studies in Organic Chemistry, Vol. 26. Elsevier Scientific
Publishers. Amsterdam (1986).
426. Pinhey, J.T., R.F. Simpson, and LL. Batey: The constituents of Olearia
References 573
heterocarpa. The structure of olearin, a diterpene dilactone of the cascarillin

group. Aust. J. Chern. 25, 2621 (1972).
427. Pinto, A.C., M.L. Patitucci, R.S. Dasilva, P.P.S. Queiroz, and A. Kelecom:
Pimarane and cleistanthane diterpenes from Velloziaceae: absolute configura-
tion and biomimetic conversion. Tetrahedron 39, 3351 (1983).
428. Piozzi, F., S. Passannanti, and M.P. Paternostro: Kaurenoid diterpenes in
Espeletia grandiflora. Phytochem. 10, 1164 (1971).
429. Proksch, P., and E. Rodriguez: Chromenes and benzofurans of the Asteraceae,
their chemistry and biological significance. Phytochem. 22, 2335 (1983).
430. Purushothaman, K.K., A. Sarada, A. Saraswathy, and J.D. Connolly:
Sempervirenic acid, a diterpene acid from Solidago sempervirens. Phyto-
chem. 22, 1042 (1983).
431. Quijano, L., J.S. Calderon, F. Gomez G., V. Rosario M., and T. Rios: Oxepane
diterpenoids and sesquiterpene lactones from "zoapatle" (Montanoa tomentosa),
a Mexican plant with oxytocic activity. Phytochem. 24, 2337 (1985).
432. Quijano, L., J.S. Calderon, F. Gomez G., V. Rosario, and T. Rios: Acyclic
precursors of the uterotonic oxepane diterpenoids of "zoapatle" (Montanoa
tomentosa). Phytochem. 24, 2741 (1985).
433. Quijano, L., J.S. Calderon, F. Gomez, J.L. Vega, and T. Rios: Diterpenes
from Stevia monardaefolia. Phytochem. 21, 1369 (1982).
434. Quijano, L., and N.H. Fischer: Sesquiterpene and diterpene lactones from
Melampodium longipilum. Phytochem. 23, 829 (1984).
435. Quijano, L., and N.H. Fischer: Two oxepane diterpene lactones from
Melampodium diffusum. Phytochem. 23, 833 (1984).
436. Quijano, L., F.R. Fronczek, and N.H. Fischer: Sesquiterpene and diterpene
lactones from Melampodium leucanthum and the molecular structure of 4(5)-
dihydromelampodin-B. Phytochem. 24, 1747 (1985).
437. Railton, I.D., B. Fellows, and C.A. West: Ent-kaurene synthesis in chloro-
plasts from higher plants. Phytochem. 23, 1261 (1984).
438. Robinson, H., and R.M. King: Eupatorieae-systematic review. In: The
Biology and Chemistry of the Compositae (Heywood, V .H., J.B. Harborne,
and B.L. Turner, eds.), Vol. 1. London: Academic Press. 1977.
439. Rogers, L.J., S.P.J. Shah, and T.W. Goodwin: Compartmentation ofbiosyn-
thesis of terpenoids in green plants. Photosynthetica 2, 184 (1968).
440. Rose, A.F.: Grindelane diterpenoids from Chrysothamnus nauseosus.
Phytochem. 19, 2689 (1980).
441. Rose, A.F., K.C. Jones, W.F. Haddon, and D.L. Dreyer: Grindelane
diterpenoid acids from Grindelia humilis: Feeding deterrency of diterpene
acids towards aphids. Phytochem. 20, 2249 (1981).
442. Rossomando, P.C., O.S. Giordano, J. Espiiieira, and P. Joseph-Nathan: A
diterpene acid from Baccharis tucumanensis. Phytochem. 24, 787 (1985).
443. Rustaiyan, A., E. Simozar, A. Ahmadi, M. Grenz, and F. Bohlmann: A
hardwickiic acid derivative from Pulicaria gnaphalodes. Phytochem. 20,
2772 (1981).
444. Ruzicka, L.: The isoprene rule and the biogenesis of terpenic compounds.
Experientia 9, 357 (1953).
445. Ruzicka, L., A. Eschenmoser, and H. Heusser: Biogenesis of steroids and
terpenic compounds. Experientia 9, 362 (1953).
574 7. References
446. St. Pyrek: Neutral diterpenoids of Helianthus annuus. J. Nat. Prod. 47, 822
(1984).
447. Sakamoto, I., K. Yamasaki, and o. Tanaka: Application of l3C NMR
spectroscopy to chemistry of plant glycosides: rebaudiosides-D and -E, new
sweet diterpene-glucosides of Stevia rebaudiana Bertoni. Chern. Pharm. Bull.
25, 3437 (1977).
448. Salmon, M., A. Ortega, G. Garcia de la Mora, and E. Angeles. A diterpenic
acid from Stevia lucida. Phytochem. 22, 1512 (1983).
449. San-Martin, A., A. Givovich, and M. Castillo: Neo-clerodane diterpenoids
from Baccharis incarum. Phytochem. 25, 264 (1986).
450. San-Martin, A., J. Rovirosa, R. Becker, and M. Castillo: Diterpenoids from
Baccharis tola. Phytochem. 19, 1985 (1980).
451. San-Martin, A., J. Rovirosa, and M. Castillo: Diterpenoids from Baccharis
tola. Phytochem. 22, 1461 (1983).
452. San-Martin, A., J. Rovirosa, C. Labbe, A. Givovich, M. Mahu and M.
Castillo: Neo-clerodane diterpenoids from Baccharis rhomboidalis. Phyto-
chern. 25, 1393 (1986).
453. Schmeda-Hirschmann, G., J. Jakupovic, V.P. Pathak, and F. Bohlmann:
Balansolide and other sesquiterpene lactones from Bejaranoa balansae.
Phytochem. 25, 2167 (1986).
454. Schmeda-Hirschmann, G., C. Zdero, R.N. Baruah, and F. Bohlmann: Further
sesquiterpene lactones from Calea and Viguiera species. Phytochem. 24, 2019
(1985).
455. Schteingart, C.D., and A.B. Pomilio: Terpenoids from Wedelia bup-
thalmiflora. Phytochem. 20, 2589 (1981).
456. Schteingart, C.D. and A.B. Pomilio: Atractyloside, toxic compound from
Wedelia glauca. J. Nat. Prod. 47, 1046 (1984).
457. Scott, A.I., F. McCapra, F. Comer, S.A. Sutherland, D.W. Young, G.A. Sim,
and G. Ferguson: Stereochemistry of the diterpenoids-IV. Structure and
stereochemistry of some polycyclic diterpenoids. Tetrahedron 20, 1339
(1964).
458. Seaman, F.: Sesquiterpene lactones as taxonomic characters in the Asteraceae.
Bot. Rev. 48, 121 (1982).
459. Seaman, F., A.J. Malcolm, and N.H. Fischer: Tomexanthin, an oxepane
diterpene from Montanoa tomentosa. Phytochem. 23, 464 (1984).
460. Sen, A.K., S.B. Mahato, and N.L. Dutta: Conyzic acid, a new diterpene resin
from Conyza stricta. Indian J. Chern. 13,504 (1975).
461. Sholichin, M., K. Yamasaki, R. Miyama, R. Yahara, and o. Tanaka:
Labdane-type diterpenes from Stevia rebaudiana. Phytochem. 19, 326 (1980).
462. Silva, M., and P.G. Sammes: A new diterpenic acid and other constituents of
Haplopappus joliosus and H. angustijolius. Phytochem. 12, 1755 (1973).
463. Singh, P., M.C. Sharma, K.C. Joshi, and F. Bohlmann: Diterpenes derived
from clerodanes from Pulicaria angustifolia. Phytochem. 24, 190 (1985).
464. Soejarto, D.D., A.D. Kinghorn, and N.R. Farnsworth: Potential sweetening
agents of plant origin. III. Organoleptic evaluation of Stevia leaf herbarium
samples for sweetness. J. Nat. Prod. 45, 590 (1982).
465. Sorensen, N .A.: Poly acetylenes and conservation of chemical characters in the
Compositae. In: The Biology and Chemistry of the Compositae (Heywood,
References 575
V.H., 1.B. Harborne, and B.L. Turner, eds.), Vol. 1. London: Academic
Press. 1977.
466. Stapel, G., H.G. Menssen, and G. Snatzke: Isolierung und strukturaufklarung
von zwei diterpenen aus Baccharis articulata. Planta Med. 38, 366. (1980).
467. Stuessy, T.F.: Heliantheae-systematic review. In: The Biology and Chemis-
try of the Compo sitae (Heywood, V.H., J.B. Harborne, and B.L. Turner,
eds.), Vol. 1. London: Academic Press. 1977.
468. Swain, T., and C.A. Williams: Heliantheae-chemical review. In: The Biology
and Chemistry of the Compo sitae (Heywood, V.H., J.B. Harborne, and B.L.
Turner, eds.), Vol. 1. London: Academic Press. 1977.
469. Tabacik, C., and M. Bard: Etude chimio-taxonomique dans Ie genre Cistus.
Phytochem. 10, 3093 (1971).
470. Tandon, S., and R.P. Rastogi: Strictic acid, a novel diterpene from Conyza
stricta. Phytochem. 18, 494 (1979).
471. Timmermann, B.N., 1.1. Hoffmann, S.D. Jolad, R.B. Bates, and T.1. Siahaan:
Diterpenoids and flavonoids from Grindelia discoidea. Phytochem. 25, 723
(1986).
472. Timmermann, B.N., 1.J. Hoffmann, S.D. Jolad, R.B. Bates, and T.1. Siahaan:
Labdane diterpenoids from Grindelia discoidea. Phytochem. 25, 1389 (1986).
473. Timmermann, B.N., 1.J. Hoffmann, S.D. Jolad, and K.H. Schram: Grindelane
diterperoids from Grindelia squarrosa and G. camporum. Phytochem. 24,
1031 (1985).
474. Timmermann, B.N., LJ. Hoffmann, S.D. Jolad, K.H. Schram, R.E. Klenck,
and R.B. Bates: Constituents of Chrysothamnus paniculatus (Compositae). 2.
Chrysolic acid, a new labdane-derived diterpene with an aromatic Bring. 1.
Org. Chern. 47,4114 (1982).
475. Timmermann, B.N., D.J. Luzbetak, 1.1. Hoffmann, S.D. Jolad, K.H. Schram,
R.B. Bates, and R.E. Klenck: Grindelane diterpenoids from Grindelia
camporum and Chrysothamnus paniculatus. Phytochem. 22, 523 (1983).
476. Tomassini, T.C.B., and M.E.O. Matos: On the natural occurrence of 15a-
tiglinoyloxy-kaur-16-en-19-oic acid. Phytochem. 18,663 (1979).
477. Tonn, C.E., P.C. Rossomando, and O.S. Giordano: Batudioic acid and
flavonoids from Baccharis tucumanensis. Phytochem. 21, 2599 (1982).
478. Tsankova, E., and F. Bohlmann: A monoterpene from Aster bakeranus.
Phytochem. 22, 1285 (1983).
479. Usubillaga, A., J. de Hernandez, N. Perez, and M. Kiriakidis: Kauranoid
diterpenes in Espeletia species. Phytochem. 12, 2999 (1973).
480. Usubillaga, A., and A. Morales: Kaurenic acids in Espeletia species.
Phytochem. 11, 1856 (1972).
481. Usubillaga, A., and A. Nakano: Kauranoid diterpenes in Ruilopezia marga-
rita. Planta Med. 35, 331 (1978).
482. Vichnewski, W., H. de Freitas Leitao Filho, R. Murari, and W. Herz:
Cinnamoylgrandifloric acid from Mikania oblongifolia. Phytochem. 16,2028
(1977).
483. Vichnewski, W., R. Murari, and W. Herz: New c1erodanes from Sym-
phiopappus itatiayensis. Phytochem. 18, 129 (1979).
484. Vis, E., and H. G. Fletcher: Stevioside. IV. Evidence that stevioside is a
sophoroside. J. Am. Chern. Soc. 78,4709 (1956).
576 7. References
485. Vlad, P.F., N.D. Ungur, and M.N. Koltsa: Cyclization and rearrangements of
diterpenoids. I. Synthesis of tetracyclic diterpenoids with a new carbon
skeleton from labdanes. Tetrahedron 39, 3947 (1983).
486. Von Carstenn-Lichterfelde, C., C. Pascual, J. Pons, R.M. Rabanal, B. Rodriguez,
and S. Valverde: Carbon-13 NMR spectra of ent-beyerane and ent-beyerene
derivatives. Tetrahedron Lett. 1975, 3569.
487. Waddell, T.G., C.B. Osborne, R. Collins, M.L Levine, M.C. Cross, LV.
Silverton, H.M. Fales, and E.A. Sokoloski: Erigerol, a new labdane diterpene
from Erigeron philadelphicus. J. Org. Chern. 48, 4450 (1983).
488. Wagenitz, G.: Systematics and phylogeny of the Compositae (Asteraceae).
Plant Syst. Evol. 125, 29 (1976).
489. Wagner, H., R. Seitz, V.M. Chari, and H. Lotter: Bacchotrcuneatin A and B, zwei
neue diterpenlactone aus Baccharis tricuneata var. tric. Tetrahedron Lett. 1977,
3039.
490. Wagner, H., R. Seitz, and H. Lotter: New furanoid ent-clerodanes from
Baccharis tricuneata. J. Org. Chern. 43, 3339 (1978).
491. Waiss, A.C., B.G. Chan, C.A. Elliger, V.H. Garrett, E.C. Carlson, and B.
Beard: Larvicidal factors contributing to host-plant resistance against sun-
flower moth. Naturwissenschaften 64, 341 (1977).
492. Warning, U., F. Bohlmann, H. Sanchez V., E. Del Rio S., and X.A.
Dominguez: New constituents of Baccharis salid/olia. Rev. Latinoamer.
Quim. 17, 199 (1986).
493. Watanabe, K., N. Ohno, H. Yoshioka, J. Gershenzon, and T.J. Mabry:
Sesquiterpene lactones and diterpenoids from Helianthus argophyllus. Phyto-
chern. 21, 709 (1982).
494. Wehrli, F.W., and T. Nishida: The use of carbon-13 nuclear magnetic
resonance spectroscopy in natural products chemistry. Fortschritte d. Chern.
org. Naturst. 36, 1 (1979).
495. Wenkert, E.: Structural and biogenetic relationships in the diterpene series.
Chern. and Ind. 1955, 282.
496. Wenkert, E., and Z. Kumazawa: Manool-derived diterpenic hydrocarbons and
related products. Chemical Communications 1968, 140.
497. West, C.A.: Biosynthesis of diterpenes. In: Biosynthesis of Isoprenoid
Compounds (Porter, J.W., and S.L. Spurgeon, eds.), Vol. 1, p. 376. New
York: John Wiley and Sons. 1981.
498. West, C.A., M.W. Dudley, and M.T. Dueber: Regulation of terpenoid
biosynthesis in higher plants. In: Topics in the Biochemistry of Natural
Products (Swain, T., and G.R. Waller, eds.). New York and London: Plenum
Press.
499. Wollenweber, E., and V.H. Dietz: Occurrence and distribution of free
flavonoid aglycones in plants. Phytochem. 20, 869 (1981).
500. Yamamura, Y., I. Masatoki, M. Niwa, Hasegawa, S. Ohba, and Y. Saito: The
isolation and structure of tricyclosolidagolactone, a new diterpene from Solidago
altissima. Tetrahedron Lett. 22, 739 (1981).
501. Yamasaki, K., H. Kohda, T. Kobayashi, N. Kaneda, R. Kasai, O. Tanaka, and
K. Nishi: Application of 13C nuclear magnetic resonance spectroscopy to
chemistry of glycosides: structures of paniculosides-I, -II, -III, -IV, and -V,
diterpene glucosides of Stevia paniculata Lag. Chern. Pharm. Bull. 25, 2895
(1977).
References 577
502. Yamasaki, K., H. Kohda, T. Kobayashi, R. Kasai, and O. Tanaka: Structures of

Stevia diterpene-glucosides: Application of 13C NMR. Tetrahedron Lett. 1976,
1005.
503. Zdero, C., F. Bohlmann, R.M. King, and H. Robinson: Diterpene glycosides
and other constituents from Argentinian Baccharis species. Phytochem. 25,
2841 (1986).
504. Zurcher, R.F.: Protonenresonanzspektroskopie und steroidstruktur. I. Das C-
19-methylsignal in funktion der substituenten. Helv. Chim. Acta 44, 1380
(1961).
505. Zurcher, R.F.: Protonenresonanzspektroskopie und steroidstruktur. II. Die
lage der C-18- und C-19-methylsignale in abhiingigkeit von den substituenten
am steroidgeriist. Helv. Chim. Acta 46,2054 (1963).
Appendix
ApPENDIX. Alphabetical Listing of Molecular Substituents including Ester Sidechains.
Name Code Structure

(1,2-dihydroxyethyl)acrylate (1,2-0H-Et)Acr
(2a-acetoxyethyl)acrylate (2-AcEt)Acr
(2a-hydroxyethyl)acrylate (2-0H-Et)Acr
2,3-diacetyloxy-2-methylbutyrate 2-Mebut-2,3-Ac
/i ro~
l"Ac
~H
2,3-dihydroxy-2-methylbutyrate 2-Mebut-2,3-0H
2,3-dihydroxyisobutyrate i-But-2,3-0H
~H
580 Appendix
ApPENDIX. (contd.).
Name Code Structure

2,3-epoxy-2-methylbutyrate Epoxyang
2,3-epoxy-n-butyrate Epoxy-n-But
~H
2-hydroxy-2-methylbutyrate 2-Mebut-2-0H
2-hydroxy-3-acetyloxy-2- 2-Mebut-2-0H-3-AC~
methylbutyrate
Ac
H
~I
2-hydroxy-3-chloro-isobutyrate i-But-2-0H-3-Cl
2-hydroxy-3-oxo-2-methylbutyrate 2-o.but-2-08-'=O ~
2-hydroxy-isobutyrate i-But-2-0H
2-methyl-butanoate 2-Mebut
Appendix 581
ApPENDIX. (contd.).
Name Code Structure

i-Val-3-Ac
~AC
3-acetoxy-isovalerate
3-furoate Fur
3-hydroxy-2-ethoxy-isobutyrate i-But-3-0H-2-0Et
~H
~H
3-hydroxy-2-methylbutyrate 2-Mebut-3-0H
3-hydroxy-isovalerate i-Val-3-0H
JlKH
3-methyl-2,3-dehydro-valerate deh-Val-3-Me
o
3-methyl-coumarate 3-Me-Coum
H
4,S-dihydroxytiglate Tig-4,S-OH
582 Appendix
ApPENDIX. (contd.).
Name Code Structure
4-acetyloxy-angelate Ang-4-Ac
4-hydroxy-5-[5-hydroxy-
tiglinoyloxy]-tiglate H
4-hydroxy-5-acetyloxytiglate Tig-4-0H-5-Ac
H
4-hydroxy-5-tiglinoyloxy-tiglate Tig-4-0H-5-Tiq
4-hydroxy-angelate Ang-4-0H
4-hydroxy-isobutyrate i-But-4-0H
Appendix 583
ApPENDIX. (contd.).
Name Code Structure
~H
4-hydroxy-methacrylate Mac-4-0H
4-hydroxy-sarracinate Sar-4-0H H
~H
4-hydroxy-tiglate Tig-4-0H
5-[5-hydroxy-tiglinoyloxy]- Tig-S-OTig-5-0H
tiglate
\:c
5-acetyloxy-tiglate Tig-5-Ac
~H
S-hydroxy-2,3-dihydro-3- dih-Sar-S-OH-3-SH
sulfydryl-sarracinate
~
S-hydroxy-tiglate Tig-S-OH
acetate Ac
584 Appendix
ApPENDIX. (contd.).
Name Code Structure

aeetyloxy OAe
~AC
aeetylsarraeinate Sarae
angelate Ang
Jy
~
anthranoate Anth
arabinoside Arab
araehinate Arae
behenate (CO(CH2)20Me Behen
~
benzoate Benz
Appendix 585
ApPENDIX. (contd.).
Name Code Structure

benzoyloxy O-Ben 0
o~
bernsteinoate O-bern
(= succinate)
cis-3-S-methylacrylate cis-Acr-S-Me
cis-cinnamate cis-Cinn
'GO ~I
~
cis-coumarate cis-Coum
~I
0
coumarate Coum
OH
~
epoxymethacrylate Epoxymac
epoxysarracinate Epoxysar
586 Appendix
ApPENDIX. (contd.).
Name Code Structure

formyloxy OCHO
r3-Galactoside Gal
H
r3-D-[6-acetoxyglucopyranoside] Glu-6-Ac
r3-D-glucopyranoside Glu
Gly
o
glycyl /~OH
hydrogen H
hydroxy OH
hydrocinnamate H-Cinn
Appendix 587
ApPENDIX. (contd.).
Name Code Structure
Jy
isobutyrate i-But
isovalerate i-Val
laurate Dodec
linoleate Linol
~H~7~
linolenate Linolen
~H2ry
malonate Mal 0 0
)l)lOH
~
methacrylate Mac
methoxy OMe
methyl Me
588 Appendix
ApPENDIX. (contd.).
Name Code Structure

methylene CH2
methylvalerate MeVal
myristate Tetradec
o
p-hydroxy-hydrocinnamate p-OH-H-Cinn
Ott
p-hydroxy-phenylacetate p-OH-Phe-Ac o ~H
~
palmitate Hexadec
Palm
peroxy O-OH
peroxy-bridge -0-0-
phenylacetate Phe-Ac
Appendix 589
ApPENDIX. (contd.).
Name Code Structure

piperidine Pip
-0
propionate Pro
~H
sarracinate Sar
senecioate Sen
AA
stearate Octadec
Stear
stearoyloxy-isovalerate
succinate Succ
o
~OH
o
tiglate Tig
590 Appendix
ApPENDIX. (contd.).
Name Code Structure

~-3-S-methylacrylate Trans-Acr-S-Me
trans-cinnamate trans-Cinn o
Compound Index
Name Number Page Numbers

Abienol 139 15, 73, 246
Abienol, 3(j-acetoxy-iso- 1151 17,75,249
Abienol, 3(j-hydroxy-ent- 436 33, 100, 305
Abienol, 6a-hydroxy-7 (j-acetoxy-12E- 1022 16, 74, 246
Abienol, 6(j, 7(j-dihydroxy-12E- 146 16, 74, 246
Abienol,6(j,7a-dihydroxy-ent- 809 33, 100, 305
Abienol, 6(j-acetoxy-7a-hydroxy-ent- 810 33, 100, 305
Abienol, 6(j-angeloyloxy-7a-acetoxy-ent- 811 33, 100, 305
Abienol, 6(j-hydroxy-12E- 144 16, 74, 246
Abienol, 6(j,18-dihydroxy-12E- 147 16, 74, 246
Abienol, 7(j-acetoxy-12E- 145 16, 74, 246
Abienol, 7(j-acetoxy-6(j-hydroxy-12E- 148 16, 74, 246
Abienol, 7(j-acetoxy-6(j-hydroxy-12a-peroxiiso- 157 16, 74, 249
Abienol, 7(j-acetoxy-6(j-hydroxy-12(j-peroxiiso- 156 16, 74, 249
Abienol, 7{J-hydroxy- 140 15, 73, 246
Abienol, 18-hydroxy- 1015 34, 101, 305
Abienol, iso- 155 16, 74, 249
Abieta-7, 13(14 )-dien-18-oic acid 616 49, 129, 356
Abieta-7,13(14)-diene, 5-acetoxy- 615 49, 129, 356
Abieta-7, 13-diene 614 49, 129, 356
Abieta-7,13-diene, 19-succinyloxy- 1054 49, 129, 356
Abietadien-3(j-ol, 7,13- 317 27, 94, 280
Abietadien-2a-ol acetate 316 27,94,280,281
Abietadien-3-one, 7,13- 318 27,94,281
Acanthoaustralide 40 10, 64, 228
Acanthoaustralide, 1,6-diacetyl- 1124 10, 65, 228
Acanthoaustralide, 17-acetoxy- 43 10, 65, 228
Acanthoaustralide, 17-hydroxy- 42 10, 65, 228
Acanthoaustralide-l-0-acetate 41 10, 65, 228
Acanthospermol-(j-galactosidopyranoside 77 12,71,238
Acritipappus lactone B 420 37, 106,313
Acritoconfert-7-en-15-oic acid, 617 49, 130, 356
16-acetoxy-17-hydroxy-
592 Compound Index

Acritoconfertic acid 472 38, 109,317
[13,14,15,16-Tetra-nor-17-hydroxy-ent-
labda-7-en-12-oic acid]
Acritoconfertic acid, 8,16,16, 17-bisoxido- 1100 50, 130, 357
Acritopappus acid 575 46, 123, 346
Acritopappus lactone A 419 36, 106, 313
Acritopappusol 574 46, 123, 346
Agathenic acid, 8,17,13, 14H-7 ,8-dehydro- 131 15, 73, 244
Agathenic acid, 8, 17H-7 ,8-dehydro- 130 15, 73, 242
Agathenic acid-16-1actone, 8, 17H-7 ,8-dehydro- 164 19,81,257
Ambreinolide, nor- 1156 21, 85,262
Aristin-19-0-arachinate, l/3-acetoxy- 149 16, 74, 246
Aristin-19-0-cis-coumarate, l/3-acetoxy- 151 16, 74, 246
Aristin-19-0-coumarate, l/3-acetoxy- 150 16, 74, 246
Articulin 1237 45, 118, 332
Articulin acetate 1238 45, 118, 332
Aspiliaparviol 1120
Athrixianone, 16, 17-dihydro-16, 17-epoxy- 757 56, 140, 373
Athrixianone, 4-carbomethoxy- 756 56, 140, 373
Athrixianone, 4-formyl- 755 56, 140, 373
Athrixianone, 4-hydroxymethyl- 754 56, 139, 373
Athrixic acid, seco- 473 38, 109,318
Atis-13-en-3/3,16a-diol, ent- 816 58, 144, 379
Atis-16-en-19-oic acid 783 58, 144, 378
Atis-16-en-19-oic acid, 784 58, 144, 378
7a-hydroxy-ent-[ occidentalic acid]
Atisan-16a-ol, ent- 853 58, 144, 378
Atisan-16/3-ol, ent- 854 58, 144, 379
Atisirene acid, 785 58, 144, 378
11a-acetoxy-[lla-acetoxy-atisirene-20-acid]
Atisirene acid, 13a-angeloyloxy- 786 58, 144, 378
Atisirene acid, 13a-isobutyryloxy- 788 58, 144, 378
Atisirene acid, 13a-isovaleryloxy- 787 58, 144, 378
14/3-acetoxy-9,11-didehydro-
[14/3-acetoxy-9,11-didehydro-atisirene-20-acid]
7a-acetoxy-9, 11-didehydro-
[7a-acetoxy-9,11-didehydroatisirene-20-acid]
Atracty ligenin 758 56, 140, 373
Atractyloside 681 53, 137, 370
Austrochaparol acetate 402 31,98,299
Austrochaparol acetate, 18-hydroxy- 408 32, 99, 302
Austrochaparol acetate, 18-oxo- 411 32, 99, 302
Austrochaparol acetate, 19-acetoxy- 409 32, 99, 302
Austrochaparol, 19-oxo- 410 32, 99, 302
Austroeupatorione 1207 38, 110,318
Compound Index 593

Austroeupatorione, 12-desoxo- 1205 38, 110,318
Austroeupatorione, 12-desoxo-2-desacety1- 1206 38, 110, 318
Austrofolin 407 32, 99, 301
Austrofolin, 3a,12-dihydroxy-12-desoxo- 413 32, 99, 301
Austrofolin, 3a-hydroxy- 412 32, 99, 301
Austrofolin-12-ol, 12-desoxo- 406 32, 99, 301
Austrofolin-15a-ol, 15,16-dihydro- 417 32,99, 303
Austrofolin-15{3-ol, 15, 16-dihydro- 418 32, 99, 303
Austroinulin 428 33, 100,304
Austroinulin, 6-0-acetyl-[Stevinsol] 429 33, 100, 304
Austroinulin, 6-angelyl-7-acetyl- 808 33, 100, 304
Austroinulin-7-0-acetate, (12Z)- 1023 17,74,246
Austroinulin-7 -O-acetate, (12Z)-6-desoxy- 1021 16, 74, 246
Ayapanone acid, 3-oxo- 468 37, 108,316
Ayapanone acid, 3a-hydroxy- 467 37, 108,316
Bacchalineol 1232 45, 118, 328
Bacchalineol malonate 508 41, 115,328
Bacchasalicyclic acid 1224 45, 118, 323
Bacchasalicyclic acid-15-0-acetate, 16-hydroxy- 1225 45, 118, 323
Bacchasalicyclic acid-15-0-[1 '-{3-xylopyranoside] 1226 45, 118, 323
Baccharis incarum compound 1 1227 45, 118, 324
Baccharis incarum neoclerodane 2 1236 45, 118, 332
Baccharis incarum compound 3 1240 45, 118, 334
Baccharis rhomboidalis neoclerodane 1 1241 45, 118, 335
Bacchascoparone 1061 46, 123, 346
Bacchofertin 521 42, 116, 330
Bacchomagellin A 1244 45, 120, 342
Bacchomagellin B 1245 45, 121,342
Bacchotricuneatin A 527 42, 119, 339
Bacchotricuneatin A [Corrected to compound 527 252 42, 119, 339
in later publication]
Bacchotricuneatin A, la-hydroxy- 1069 44, 119, 339
Bacchotricuneatin A, 1a-acetyl- 1257 45, 120, 340
Bacchotricuneatin A, 6{3-hydroxy-7,8-dehydro- 972 42, 119, 341
Bacchotricuneatin A, 7a-hydroxy- 1258 45, 120, 340
Bacchotricuneatin B 529 42, 120, 342
Bacchotricuneatin B, 2a-angeloyloxy- 968 42, 120, 342
Bacchotricuneatin B, 7{3-angeloyloxy- 530 42, 120,342
Bacchotricuneatin C 528 42, 119, 340
Bacchotricuneatin D 509 41, 115,328
Bacchotricuneatin, 2a-angeloyloxy-3a- 533 42, 120, 342
[2-methylbutyryloxy]-3,4{3H-
Bacchotricuneatin, 531 42, 120, 342
2a-angeloy10xy-3a-senecioyloxy-3 ,4{3H-
594 Compound Index

Bacchotricuneatin, 532 42, 120, 342
2a-senecioyloxy-3a-angeloyloxy-3,4/3H-
Barticulidiol 1233 45, 118, 328
Barticulidiol, 18-acetoxy-19-malonyloxy- 510 41, 115,328
Batudioic acid 110 14, 72, 242
Bedfordia diterpene alcohol 236 39, 113, 324
Bedfordia diterpene alcohol, iso- 237 47, 124
Beyer-15-en-12a, 19-diol, ent- 817 57, 142, 376
Beyer-15-en-17,19-diol, 771 57, 142,376
ent-[17-hydroxymonogynol]
Beyer-15-en-18,19-diol, ent- 772 57, 142, 376
Beyer-15-en-18-o1, ent- 766 57, 142, 375
Beyer-15-en-19-oic acid, 3a-tigloyloxy-ent- 776 57, 142,375
Beyer-15-en-19-oic acid, ent-[stach-15-en-19-oic 774 57, 142, 375
acid; beyerenic acid]
Beyer-15-en-19-oic acid, 3a-hydroxy-ent- 775 57, 142, 375
Beyer-15-en-19-o1, ent-[Erythroxylol-A] 765 57, 142,375
Beyer-15-en-3a, 12/3-diol, ent- 768 57, 142, 375
Beyer-15-en-3a-ol, ent- 764 57, 142, 375
Beyer-15-ene, 19-oxo-ent-[20-oxostachene] 773 57, 142, 375
Beyer-15-ene, 4a-hydroxy-19-nor-ent- 782 57, 143,378
Beyer-9(11),15-dien-19-oic acid, 778 57, 142, 376
3a-tigloyloxy-ent-
Beyer-9(1l) , 15-dien-19-oic acid, ent- 777 57, 142,376
Beyeran-18-o1, 15/3,16/3-epoxy-ent- 779 57, 142,377
Beyeran-19-o1, 15,16-epoxy-ent- 780 57, 142, 377
[erythroxylol A-14,15-oxide]
Biformen, 3-oxo-12,13E- 136 15, 73, 245
Biformen, 3a-hydroxy-12,13E- 133 15, 73, 245
Biformen, 3/3-hydroxy-12, 13E- 134 15,73,245
Biformen, 3/3-acetoxy-12,13E- 135 15, 73, 245
Biformene, ent- 422 33, 100,303
Biformene, 3a, 14, 15-trihydroxy-12E, 1186 36, 102, 305
14,15-dihydro-ent-
Biformene, 12,13E-ent- 430 33, 100, 305
Biformene, 18-oxo-ent- 423 33, 100, 303
Biformen, 12,13E- 132 15,73,244
Bincatriol 1222 44, 118, 322
Brickellidiffusic acid angelate 97 13, 72, 242
Brickellidiffusic acid spiro ketal lactone, 215 20,81,258
2a-angeloyloxy-17,O-dihydro-
Brickellidiffusic acid spiro ketal lactone, 216 20, 82, 258
2a-angeloyloxy-17a-hydroxy-17,O-dihydro-
Brickellidiffusic acid spiro ketal lactone, 218 20, 82, 258
2a-hydroxy-17,O-dihydro-
Compound Index 595

Brickellidiffusic acid spiro ketal lactone, 217 20, 82,258
2a-angeloyloxy-17{j-hydroxy-17 ,O-dihydro-
Carboxyatractyloside 678 53, 137,369
Carterochaeta acid 211 19, 80, 256
Carterochaetal, 213 19, 80, 256
16-acetoxy-14-oxo-13, 14H-12, 13-dehydro-
Carterochaetal, 16-oxo- 207 19, 80, 256
Carterochaetal, 16-oxo-13, 14H-12, 13-dehydro- 212 19, 80, 256
Carterochaetol 210 19, 80, 256
Carterochaetol acetate, 16-acetoxy- 205 19, 80, 256
Carterochaetol, 16-hydroxy- 203 19, 80, 256
Carterochaetol, 208 19,81,257
16-hydroxy-13, 14H-13a, 14a-epoxy-
Carterochaetol, 209 19,81,257
16-hydroxy-13, 14H-13{j, 14{j-epoxy-
Carterochaetol, 16-oxo- 206 19, 80, 256
Carterothaminotriol 82 13,71,240
Carterothaminotriol-14, 15-0-diacetate 84 13, 71, 240
Carterothaminotriol-15-0-acetate 83 13, 71, 240
Carterothamnotriol, 14{j- 94 13,72,247
Carterothamnotriol-14,15-0-diacetate, 14{j- 96* 75, 247
Carterothamnotriol-I5-0-acetate, 14{j- 95* 6, 75, 247
Carterochaetol, 16-acetoxy- 204 19, 80, 256
Cativic acid 118 14, 72, 243
Cativic acid methyl ester, 3a-hydroxy- 992 14, 72, 245
Cativic acid, 18-angeloyloxy- 122 15, 73, 244
Cativic acid, 18-angeloyloxy-13,14-dehydro- 101 13, 72, 241
Cativic acid, 18-tigloyloxy- 123 15, 73, 244
Cativic acid, 18-tigloyloxy-13,14-dehydro- 102 13, 72, 241
Cativic acid, 2-angeloyloxy-13,14Z-dehydro- 100 13,72,241
Cativic acid, 2a,3a-[angeloyloxy- & 2-hydroxy- 99 13, 72, 243
2-methylbutyryloxy ]-7 a-cis-cinnamoyloxy-
Cativic acid, 2a,3a-[angeloyloxy-& 2-hydroxy- 98 13, 72, 243
2-methylbutyry loxy ]-7 a-trans-cinnamoyloxy-
Cativic acid, 2a,3a-dihydroxy- 124 15,71,238
Cativic acid, 2a-angeloyloxy-3a-hydroxy- 107 14, 72, 242
(13Z)-13,14-didehydro-
(13Z)-13,14-didehydro-8(17)-
Cativic acid, 2a-hydroxy-3a- 125 15,71,238
[2-hydroxy-2-methylbutyryloxy]-
Cativic acid, 2{j,3{j-dihydroxy-ent- 1196 36, 102
Cativic acid, 3-oxo- 129 15,71,238
[Brickellia acid C]
* Acetylation products of compound 94. These compound numbers were applied to other
structures, but these earlier uses were not removed.
596 Compound Index

(13Z)-13,14-didehydro-
Cativic acid, 3a-angeloyloxy-2a-hydroxy- 108 14,72,240
(13Z)-13,14-didehydro-8(17)-
13,14Z-dehydro-
Cativic acid, 3a-cis-cinnamoyloxy-2a-hydroxy- 128 15, 73, 244
Cativic acid, 3a-cis-cinnamoyloxy-2a-hydroxy- 105 14, 72, 241
13,14Z-dehydro-
Cativic acid, 3a-hydroxy- 991 14,72,245
Cativic acid, 3a-trans-cinnamoyloxy- 127 15, 73, 244
2a-hydroxy-
Cativic acid, 3a-trans-cinnamoyloxy-2a-hydroxy- 104 14, 72, 241
13,14Z-dehydro-
Cativin-3,15-dioic acid, 3,4-seco- 220 20, 83, 259
Centipedic acid 60 11,67,232
Chiliolide, 3a,5a-dihydroxy- 1212 39, 111,320
Chiliolide, 3a-hydroxy-5,6-dehydro- 1213 39, 111,320
Chiliolide, 3a-hydroxy-5~, lO~-epoxy- 1214 39, 111,320
Chiliolide aldehyde, seco- 1215 39,111,320
Chiliolide acid, seco- 1216 39, 111,321
Chiliolide, 19-hydroxy-seco- 1217 39, 112, 321
Chiliolide acid methyl ester, 19-hydroxy-seco- 1218 39, 112, 321
Chiliolide lactone, seco- 1219 39, 112, 321
Chiliotrin, seco- 1220 39, 112, 321
Chiliolide lactone, iso- 1221 39, 113, 321
Chiliomarin 1246 47, 124, 349
Chrysolic acid 271 24,89,272
Chrysothane [Strictanonic acid] 223 20, 83, 259
Cleistanth-12-en-11-one, 608 49, 128, 355
14~, 15~-dihydroxy-16, 17-oxido-
Cleistanth-12-en-11-one, 15,16-epoxy- 601 49, 128, 354
Cleistanth-12-en-l1-one, 605 49, 128, 354
17-acetoxy-14~-hydroxy-15, 16-epoxy-
Cleistanth-12-en-11-one, 17 -acetoxy-15, 16-epoxy- 603 49, 128, 354
17-acetoxy-15,16-epoxy-iso-
17-acetoxy-3,4, 15, 16-diepoxy-iso-
Cleistanth-12-en-ll-one, 606 49, 128, 354
17 -acetoxy -3a-angeloyloxy -15, 16-epoxy-
Cleistanth-12-en-ll-one, 604 49, 128,354
3a-angeloyloxy-15, 16-epoxy-
Cleistanth-12-en-17 -ai, l1-oxo- 607 49, 128, 354
8,9,15,16-diepoxy-
Cleistanth-12-en-17-al, 15, 16-epoxy-11-oxo- 602 49, 128,354
Cleroda-1 ,3, 13(16), 14-tetraen-18-oic acid, 512 41, 115,322
15,16-epoxy-ent-
Cleroda-13(14)-ene-15,16-olide, 3a,4: 18, 1087 24,89,270
Compound Index 597

19-diepoxy-18{3,19a-dihydroxy-cis-
Cleroda -13 (14 )-ene-15 , 16-olide, 1089 24, 89, 271
3a,4: 18, 19-diepoxy-19a-hydroxy-cis-
Cleroda-13(14 )-ene-15, 16-olide, 1090 24, 89, 271
3a,4{3, 19a-trihydroxy-18, 19-epoxy-cis-
Cleroda-13(14)-ene-15, 16: 18, 19-diolide, 1088 24,89,270
3a,4-epoxy-19a-hydroxy-cis-
Cleroda-3, 13( 14 )-diene-15, 16-olide, 1084 24, 89, 269
18,19-dihydroxy-cis-
Cleroda-3, 13(14 )-diene-15, 16-olide, 1086 24, 89, 270
18,19-epoxy-19a-hydroxy-cis-
Cleroda-3, 13(14)-diene-15, 16-o1ide, 1083 24, 89, 269
6a,18-dihydroxy-cis-
Cleroda-3, 13(14 )-diene-15, 16-o1ide-19-oic ester, 1091 24,89,269
19-0-a- L-arabinopyranosy l-cis-
Cleroda-3, 13(14 )-diene-15, 16: 18, 19-diolide, cis- 1085 24, 89, 270
Cleroda-3, 13(14)-diene-15, 16: 18,6a-diolide, 1092 24, 89, 271
2{3,6a-dihydroxy-cis-
Cleroda-3, 13(16), 14-trien-15, 16-oxide, 17-oxo- 967 41, 115,328
Cleroda-3, 13(16), 14-trien-18,6a-olide, 583 47, 124,348
15,16-epoxy-cis-ent-
Cleroda-3, 13(16), 14-triene, 15, 16-epoxy-cis- 578 47, 124, 347
Cleroda-3, 13(16), 14-triene, 580 47, 124, 347
18-acetoxy-15,16-epoxy-cis-
Cleroda-3, 13(16), 14-triene, 579 47, 124, 347
18-hydroxy-15, 16-epoxy-cis-
Cleroda-3, 13(16), 14-triene,6a, 581 47, 124, 347
18-dihydroxy-15, 16-epoxy-cis-ent-
Cleroda-3, 13(16), 14-triene,6a-hydroxy- 582 47, 124,347
18-acetoxy-15,16-epoxy-cis-
Cleroda-3, 13E-dien-15-oic acid, 18-acetoxy-cis- 1055 47, 124,348
Cleroda-3, 13E-dien-15-oic acid, 18-hydroxy-cis- 1056 47, 124,348
Cleroda-3-en-15, 16, 18,6a-diolide, 585 47, 124,348
2{3-hydroxy-cis-
Cleroda-3-en-15, 16, 18,6a-diolide, cis- 584 47, 124,348
Cleroda-3-en-15-oic acid, 18-hydroxy-cis- 1057 47, 124,349
Cleroda-3-en-15-oic acid, 19-hydroxy- 1058 47, 124,349
Clerodan-15-oic acid, 3,4-dehydro-cis- 257 22, 87, 266
Communic acid 137 15, 73, 245
Communic acid, 7a-acetoxy-trans- 138 15, 73, 245
Conycephaloide 525 42, 119, 339
Conycephaloide, 12-epi- 969 42, 119, 340
Conycephaloide, 12-epi-8{3, 17 -dihydro- 970 42, 119, 340
Conycephaloide, 7-hydroxy-17 -oxo- 526 42, 119, 339
7, 8-dehydro-8, 17 -dihydro-
Conypododiol 61 11,67,232
Conyscabraic acid, 5,6-dehydro- 918 46, 122, 344
Conyscabraic acid, 5,6-dehydroiso- 917 46, 122, 344
Conyscabraic acid, 5a-hydroxy- 920 46, 122, 345
598 Compound Index

Conyscabraic acid, 5a-hydroxyiso- 919 46, 122, 344
Conyzic acid 405 32, 99, 301
Cordobic acid 1140 17,71,239
Cordobic acid-18-acetate 1141 17,71,239
Cordobic acid, 7-epi- 1142 17,71,239
Cupressen-18-oic acid 325 28, 95, 284
Dimerobrasiolide 64 11,68,233
Daniellic acid 839 31,99,300
Daniellic acid, 3a-hydroxy- 840 31,99, 300
Daniellol 403 31,98,299
Daniellol, 18-hydroxy- 841 31,99, 300
Daniellol, 3a,18-dihydroxy-19-deoxy- 842 32,99, 300
Darutigenol 591 48, 126, 353
Darutigenol-3a-glucoside 592 48, 126,353
Dimeroaperatate, methyl- 63 11,68,232
Dimeroaperatic acid 62 11,68,232
Dimerobrasiolide 64 11,68,233
Discoidic acid 1145 17,75,244
Doronicoside D 945 53, 137,369
Du1coside A 686 53, 139, 371
Du1coside B 687 53, 139, 371
Elongatolide A [Solidagolactone IV; 545 23, 88, 265
6{j-hydroxy -solidagolactone]
Elongatolide B 546 23, 88, 265
Elongatolide D [Solidagolactone VI 553 23, 88, 266
(structure no. 555)]
Elongatolide E [Solidago lactone VII] 260 22, 87, 266
Eperuic acid, 2a-iso-valeroyloxy- 358 29,97,291
Erigerol 461 34, 101, 308
[1 ,6{j-dihydroxy-7 ,8{j-epoxydihydrogrendelyl
ester of 3,3-dimethylacrylic acid]
Erythroxa-3, 15-dien-18-oic acid 976 50, 131, 357
Erythroxylol A-malonate 769 57, 142,375
Eupatalbin 805 59, 146, 382
Eupatoralbin 806 59, 146, 382
Evillosin 938 20, 82, 259
Ferruginol 319 27,94,281
Geranylascaridol, a-l0, IIH-lO, Il-dihydroxy-9- 1101 12, 69, 236
Furosolidagonol 1126 11,67,232
Furosolidagonone 1125 11,67,232
Furosolidagonone, 13-hydroxy- 1127 11,67,232
Furosolidagonone, 1129 11,68,233
l-oxo-2,3-dehydro-l ,2,3 ,20-tetrahydro-
15-peroxy-13, 14E-dehydro-14, 15-dihydro-
20-oxo-l ,2-epoxy-l ,2,3 ,20-tetrahydro-
GeranyiascaridoI, {j-1O, lIH-lO, II-dihydroxy-9- 72 12, 69, 235
Compound Index 599

Geranylascaridol, a-1O, 1IH-1O, II-dihydroxy-9- 1101 12, 69, 236
Geranylcurcumen, 9- 70 12, 69, 235
Geranylcurcumen, 10, IIH-1O, I1-dihydroxy-9- 71 12, 69, 235
Geranylgearanal, 12-oxo- 1119 8,62,224
Gerany1geranial 17 8, 62, 223
Geranylgeranial, 4-hydroxy- 18 8, 62, 223
Geranylgeraniol acetate, 12,19-dihydroxy- 12 8, 62, 222
Gerany1geraniol, 12, 18-dihydroxy-6, 7Z- 22 8,62,224
Geranylgeraniol, 12,19-dihydroxy- 11 8, 62, 222
Geranylgeraniol, 16 8,62,223
14, 15-dihydro-4, 14, 15-trihydroxy-
Geranylgeraniol, 16-hydroxy- 13 8, 62, 223
Geranylgeraniol, 17-hydroxy-18-acetoxy- 1118 8, 62, 223
Geranylgeraniol, 21 8,62,224
19-hydroxy-12-oxo-l0, II-dihydro-
Gerany 1geraniol, 13 -oxo-2, 3-dihydro- 20 8,62,223
Gerany linalool, 36 9, 63, 226
14, 15-dihydro-13, 14, 15, 17-teradehydro-
Geranylgeraniol-20-acid lactone, 1133 11,68,233
18-acetoxy-6,7, 10, I1-tetrahydro-
Geranylgeraniol-20-acid lactone, 17-hydroxy- 1134 11,68,233
18, 19-diacetoxy-6,7, 10, I1-tetrahydro-
Gerany llinalool 23 8, 62, 224
Geranyllinalool, 12-oxo- 32 9, 63, 225
Geranyllinalool, 1123 9, 63, 226
12-oxo-15-hydroxy-13,14E-dehydro-
1O,11,14,15-tetrahydro-
Geranyllinalool, 13-hydroxy 24 8, 62, 225
Geranyllinalool, 13-acetoxy- 25 8, 62, 225
Geranyllinalool, 13-acetoxy-5-hydroxy- 31 9, 63, 225
Geranyllinalool, 13-oxo- 33 9, 63, 225
Geranyllinalool, 13-oxo-14,15-epoxy- 34 9, 63, 225
Geranyllinalool, 14, 15-dihydro-14, 15-dihydroxy- 37 9, 63, 226
Geranyllinalool, 39 9, 63, 226
14, 15-dihydroxy-9-acetoxy-14, 15-dihydro-
Gerany llinalool, 35 9, 63, 226
15-hydroxy-13, 14-dehydro-14, 15-dihydro-
Geranyllinalool, 5,14, 15-trihydroxy- 38 9, 63, 226
14,15-dihydro-
Gerany llinalool, 5, 9-diacetoxy- 30 9, 63, 225
Geranyllinalool, 5-hydroxy- 28 8, 63, 225
Geranyllinalool, 9-acetoxy-5-hydroxy- 29 9, 63, 225
Geranyllinalool, 9-hydroxy- 26 8, 63, 225
Geranyllinalool, 12-oxo-1O,11-dihydro- 1122 9, 63, 225
Geranylneral 5 7,60,219
Geranylneral, 12-oxo- 1111 7,60,219
600 Compound Index

Geranylnerol 1 7,60,219
Geranylnerol acetate, 1005 7,61,221
19-acetoxy-15-hydroxy-14-oxo-
Geranylnerol, 979 7, 61, 221
6, 7-epoxy-19-hydroxy-12-oxo-6, 7-dihydro-
Geranylnerol, 8,12, 19-trihydroxy- 948 7,60,220
Geranylnerol, 9,17-dihydroxy- 1116 8,61,220
Geranylnerol, 9,7, 19-trihydroxy- 1117 8,61,220
Gerany Inerol, 12, 19, 20-trihydroxy -14-methy lene- 9 9,64,227
Geranylnerol, 12,20-dihydroxy-16-oxo- 8 7,60,220
Geranylnerol, 12,20-dihydroxy-19-acetoxy- 15 7,60,220
Geranylnerol, 12,20-dihydroxy-19-acetoxy- 10 9,64,227
14-methylene-
Geranylnerol, 15,19-dihydroxy-14-oxo- 1004 5,7,61,221
Geranylnerol, 16,18,19-trihydroxy- 957 7,60,220
Geranylnerol, 17, 18-dihydroxy- 1109 7,60,219
Geranylnerol, 17, 18,20-trihydroxy- 1110 7,60,219
Geranylnerol, 18-hydroxy- 2 7,60,219
Geranylnerol, 18, 19-diacetoxy-17 ,20-dihydroxy- 1112 8,60,220
Geranylnerol, 18,19,20-triacetoxy-17-hydroxy- 1113 8,60,220
Geranylnerol, 18-acetoxy-17,20-dihydroxy- 1114 8,60,220
Geranylnerol, 19-acetoxy-17,20-dihydroxy- 1115 8,61,220
Gerany Inerol, 19-acetoxy-20-hydroxy- 984 7,60,219
Geranylnerol, 19-hydroxy-12-oxo- 978 7,60,221
Geranylnerol, 20-acetoxy-1O,II-epoxy- 1020 7,61,222
1O,11-dihydro-9-hydroxy-
Geranylnerol, 17,20-dihydroxy- 4 7,60,219
Geranylnerol, 19-hydroxy-13-oxo- 7 7,60,220
Geranylnerol, 20-hydroxy- 3 7,60,219
Gerany Inerol-19-oic acid 1002 7,60,219
Gerany Inerol-19-oic acid, l-acety1- 1003 7,60,219
Geranylnerol-6,7-epoxide, 8,12, 19-trihydroxy- 949 7,61,221
Gerranyllinalool, 13-hydroxy- 24 8, 62, 225
Geranyl-a-terpinene, 9- 68 12, 69, 235
Geranyl-a-terpinene, 10, IIH-lO, II-dihydroxy-9- 69 12, 69, 235
Geranyl-a-terpineol, 9- 1138 12,69,234
Gnaphalene, 8a,13a-dihydroxy- 586 47, 125,350
Gnaphala-13(16),14-diene, 8a-hydroxy- 1152 17,75,250
Gochnatoic acid-17 -O-phenylacetate 522 42, 116,326
Gochnatol-17-0-acetate 487 40, 114,326
Grandifloric acid 646 51, 132,359
[15a-hydroxy-ent-kaur-16-en-19-oic acid]
Grinde-6,8(17)-dienic acid 166 17,76,251
Grindelate, methyl- 1153 18,77,252
Grindelate, methyl-4/l-hydroxy-6-oxo-19-nor- 1154 20, 83, 260
Grindelic acid 167 17,76,251
Grindelic acid, 17 -[2-methy Ibutyry loxy ]- 178 18, 76, 252
Grindelic acid, 17-acetoxy- 174 17,76,252
Compound Index 601

Grindelic acid, 17-grindeloxy- 956 18, 78, 254
Grindelic acid, 17-hydroxy-[Oxygrindelic acid] 173 17,76,251
Grindelic acid, 17-isobutyryloxy- 176 18, 76, 252
Grindelic acid, 17-isovaleryloxy- 177 18, 76, 252
Grindelic acid, 17-methoxy- 179 18, 76, 252
Grindelic acid, 17-propionyloxy- 175 17,76,252
Grindelic acid, 18-hydroxy- 188 18,77,252
Grindelic acid, 19-[2-methylbutyryloxy]- 184 18,77,252
Grindelic acid, 19-acetoxy- 181 18, 76, 252
Grindelic acid, 19-acetoxy-6-oxo- 190 18,77,252
Grindelic acid, 19-hydroxy- 180 18, 76, 252
Grindelic acid, 19-isobutyryloxy- 183 18, 76, 254
Grindelic acid, 19-isova1ery1oxy- 182 18, 76, 252
Grindelic acid, 19-oic- 187 18,77,252
Grindelic acid, 19-oxo- 186 18, 77, 252
Grindelic acid, 19-succinyloxy- 185 18, 77, 252
Grindelic acid, 1a-hydroxy- 168 17,76,251
Grindelic acid, 3a-hydroxy- 1035 18, 77, 252
Grindelic acid, 3J3-hydroxy- 169 17,76,251
Grindelic acid, 4a-formyloxy-19-nor- 222 20,83,260
Grindelic acid, 4a-hydroxy-19-nor- 221 20,83,260
Grindelic acid, 6-oxo- 189 18,77,252
Grindelic acid, 6a-formyloxy- 171 17,76,251
Grindelic acid, 6a-hydroxy- 170 17,76,251
Grindelic acid, 6J3-hydroxy- 172 17,76,251
Grindelic acid, 7a,8a-epoxy-7,8-dihydro- 192 18,77,253
Grindelic acid, 165 17,76,251
7a-hydroxy-7 ,8-dihydro-8( 17)-dehydro-
Grindelic acid, 7J3, 8J3-epoxy-7, 8-dihydro- 191 18,77,253
Grindelic acid, 1036 18,77,251
7J3-hydroxy-8(l7)-dihydro-7 ,8-dehydro-
Grindelic acid, iso- 955 18, 76, 254
Grinde1ic acid -15 -O-arabinoside 1060,1187 18, 78, 254
Grindelistrictic acid 224 21,84,260
Guamaic acid 1164 35, 101,285
Guteriolide 270 23, 88, 268
Gutierrezial 845 47, 125
Gutierrezianol acid-[2 I -methy1butyrate] 160 16,74,250
Gutierrezianol acid-isobutyrate 161 16, 74, 250
Gutierreziano1 acid-isovalerate 162 16, 74, 250
Gutierrezia sphaerocephala 95 17,75,248
labdane-a-L-arabino-pyranoside 1
labdane-a-L-arabino-pyranoside 2
labdane-J3-D-xylo-pyranoside 3
labdane-J3-D-xylo-pyranoside 5
602 Compound Index

labdane-I3-D-xylo-pyranoside 6
Gutierrezia spathulata ent-labdane 4 l194 36, 102, 311
Gutierrezia spathulata ent-labdane 5 l195 36, 102, 311
Gutiesolbriolide, 17-hydroxy- 1130 l1, 68, 233
Gutiesolbriolide, 10E, 17-hydroxy- 1131 l1, 68, 233
Gutiesolbriolide, 17-acetoxy- 1132 11,68,233
Gutiesolbriolide, 17-hydroxyiso- 1135 11,68,234
Gutiesolbriolide, 17 -acetoxyiso- 1136 11,68; 234
Gymnospermin 80 13, 70, 237
Haplociliatic acid 505 41, 115,327
Haplopappate, monomethyl- 577 47, 124, 348
Haplopappic acid 576 47, 124,348
Haplopappus pauciden-tatus compound 27 1208 38, 110,319
Haplopappus pectinatus ent-labdane 13 1175 35, 101,293
Haplopappus pectinatus ent-labdane 14 1176 35, 102, 293
Haplopappus pectinatus ent-labdane 15 l177 35, 102, 293
Haplopappus pectinatus ent-labdane 17 l178 35, 102,293
Haplopappus pectinatus ent-labdane 16 360 30,97,292
Hardwickiic acid lactone, 7-oxo-6a-hydroxy 523 42, 116, 330
Hardwickiic acid, (-)- 511 41, l15, 328
Hardwickiic acid, 12a-[2-methylbutyryloxy]-( -)- 953 41, 115,329
Hardwickiic acid, 15,16H-15-oxo- 558 43, 116,332
Hartwrightia acid 462 36, 105, 312
Hautriwaic acid 1033 44, 117,336
Hautriwaic acid lactone 520 42, 116, 330
Hautriwaic acid, 1,2-dehydro- 1070 44, 117,322
Hautriwaic acid, 1O-0-methyl 901 41, 115,328
Hautriwaic acid, 13,14,15,16-tetranor- lqQ~ 46, 123, 347
1,2-dehydro
Haulriwaic acid, 14a, 15a-epoxy- 907 44, 117,334
16-oxo-13, 14, 15, 16-tetrahydro-
Hautriwaic acid, 14(3,15(3-epoxy- 908 44, 117,334
16-oxo-13, 14, 15, 16-tetrahydro-
Hautriwaic acid, 15a-hydroxy- 905 43, 117,334
16-oxo-15,16-dihydro-
Hautriwaic acid, 15(3-hydroxy- 906 44, 117,334
Hautriwaic acid, 16a-acetoxy-19-0-acetyl- 909 43, 116,332
Hautriwaic acid, 19-0-acetyl-1,2-dehydro- 911 41, 115,322
Hautriwaic acid, 19-0-angelyl- 902 41, l15, 328
Hautriwaic acid, 19-0-isovaleryl- 903 41, 115,328
Hautriwaic acid, 19-acetyl- 900 41, 115,328
Hautriwaic acid, 19-oxo- 904 41, 115,328
Hautriwaic acid, 2(3-hydroxy- 1034 44, 117,329
Hautriwaic acid-19-lactone, 12a-hydroxy- 950 42, 116, 330
Hautriwaic acid-19-lactone, 7a,12a-dihydroxy- 951 42, 116, 330
Compound Index 603

Hautriwaiic acid, 16{1-acetoxy-19-0-acetyl- 910 43, 116, 332
Hebec1inolide 999 59, 149, 384
Helicallen-16-al 66 12, 69, 234
Helicallen-16-oic acid, 14,15-dihydro- 67 12, 69, 234
Helicallen-16-o1 65 12, 69, 234
Helifulvan-19-oic acid 797 59, 146, 382
Helifulvan-19-oic-acid, lla-acetoxy- 799 59, 146, 382
Helifulvan-19-oic-acid, 11a-hydroxy- 798 59, 146, 382
Helifulvan-19-o1 796 58, 146, 382
Hexa-deca-2E,6E, lOE, 14-tetraene, 954 8,62,223
I-hydroxy-ll-carboxy-3, 7, 15-trimethyl-
Ichthyouleolide 49 10,66,229
Ichthyouleolide, 54 10,66, 230
14-hydroxy-15,17-dehydro-14,15-dihydro-
Ichthyouleolide, 53 10, 66, 230
14-peroxy-15, 17-dehydro-14, 15-dihydro-
Ichthyouleolide, 52 10,66,229
15-hydroxy-13,14t-dehydro-14-15-dihydro-
Ichthyouleolide, 51 10,66,229
15-peroxy-13,14t-dehydro-14-15-dihydro-
Ichthyouleolide, 19-acetoxy- 50 10, 66, 229
Imbricatol-angelate, 3-hydroxy- 516 41, 115,329
Imbricatol-isovalerate, 3-hydroxy- 514 41, 115,329
Imbricatol-a-methy 1butyrate, 3-hydroxy- 515 41, 115,329
Inulaefol 804 59, 148, 384
Inuroyleanol 320 27,94,281
Isoacanthoaustralide, 17-acetoxy- 47 10, 65, 229
Isoacanthoaustralide, 17-hydroxy- 46 10, 65, 229
Isoacanthoaustralide, 1-0-acetate 48 10,65,229
Isocembrene, 15-hydroxy-13, 18H- 73 12, 69, 236
Jesromotetrol, 3{1-acetoxy- 1162 27,93,278
Jesromotetrol, 3{1, 19-diacetoxy- 1161 27, 93, 278
Jhanic acid 940 59, 149, 384
Jhanidiol 197 19, 79, 255
Jhanidiol-19-monoacetate 198 19, 79, 255
Jhanidiol-diacetate 199 19, 79, 255
Jhanilactone 941 21, 85,262
Jhanol 195 19, 79, 255
Jhanol acetate 196 19, 79, 255
Julslimdiolone, 19-nor- 309 27,93,280
Julslimtetrol 308 26,92,277
Junceanol W 1072 28, 94, 283
Junceanol X 1073 28, 94, 283
Junceanol Y 1074 28, 94, 283
Junceic acid epoxide 1071 44, 117,336
Kaurenic acid, 18-angeloyloxy-ent- 939 50, 132, 358
Kaur-ll-en-19-oic acid, 16a-hydroxy-ent- 724 55, 135,362
604 Compound Index

Kaur-15(16)-en-19-oic acid, 708 54, 134, 364
3a-isobutyryloxy-9{3-hydroxy-ent-
[3a-Isobutyryloxy-9{3-hydroxy-
9, II-dihydro-polymnia acid]
Kaur-15(16)-en-19-oic acid, 707 54, 134, 364
3a-isovaleryloxy-9{3-hydroxy-ent-
[3a-Isovaleryloxy-9{3-hydroxy-
9,1l-dihydro-polymnia acid]
Kaur-15-en-17, 19-dioic acid, ent- 703 54, 134, 364
Kaur-15-en-19-al, (-)- 946 54, 134, 364
Kaurenal,9,1l-dehydro-ent 942 56, 136, 362
Kaur-15-en-19-oic acid, 701 54, 134,364
17 -hydroxy-ent-[17 -hydroxy-ent-isokaur-
15(16)-en-19-oic acid]
Kaur-15-en-19-oic acid, 17-oxo-ent- 702 54, 134,364
Kaur-15-en-19-oic acid, ent- 700 54, 134, 364
Kaur-15-ene, 17, 19-dihydroxy-ent- 698 53, 134, 364
Kaur-15-ene, 17-hydroxy-19- 699 53, 134, 364
[p-hydroxy-hydrocinnamoyloxy]-
[17 -hydroxy-19-[p-hydroxy-hydro-
cinnamoy loxy ]-isokaurene]
Kaur-15-ene, 697 53, 134, 364
17-hydroxy-ent-[17-hydroxy-isokaurene]
Kaur-16-ene, 18-acetoxy-ent- 626 50, 132, 358
Kaur-16-en-19-oate, 661 52, 133, 360
methyl-15a-hydroxy-ent-
[grandifloric acid methylester]
Kaur-16-en-19-oic acid glycol ester, ent- 627 50, 132,358
Kaur-16-en-19-oic acid thujanol ester, ent- 850 56, 136, 369
Kaur-16-en-19-oic acid, 11{3,15{3-dihydroxy-ent- 671 52, 133, 361
Kaur-16-en-19-oic acid, 1260 52, 136, 361
11{3, 12{3, 15{3-trihydroxy-ent-
Kaur-16-en-19-oic acid, l1{3-acetoxy-ent- 640 51, 132,358
Kaur-16-en-19-oic acid, 11{3-hydroxy-15-oxo-ent- 674 52, 134, 361
Kaur-16-en-19-oic acid, 672 52, 133, 361
11{3-hydroxy-15{3-acetoxy-ent-
Kaur-16-en-19-oic acid, 12a-acetoxy-ent- 642 51, 132,359
Kaur-16-en-19-oic acid, 12a-hydroxy-ent- 641 51, 132,359
Kaur-16-en-19-oic acid, 653 51, 133,359
15a-[2-methylacryloyloxy]-ent-
Kaur-16-en-19-oic acid, 15a-acetoxy-ent- 648 51, 132,359
Kaur-16-en-19-oic acid, 15a-angeloyloxy-ent- 649 51, 133,359
Kaur-16-en-19-oic acid, 15a-benzoyloxy-ent- 657 51, 133,359
Kaur-16-en-19-oic acid, 655 51, 133,359
15a-cinnamoyloxy-ent-
[cinnamoyloxy-grandifloric acid]
Kaur-16-en-19-oic acid, 15a-isobutyroyloxy-ent- 654 51, 133,359
Kaur-16-en-19-oic acid, 15a-isovaleryloxy-ent- 652 51, 133,359
Compound Index 605

Kaur-16-en-19-oic acid, 15a-senecioyloxy-ent- 651 51, 133,359
Kaur-16-en-19-oic acid, 15a-tigloyloxy-ent- 650 51, l33, 359
Kaur-16-en-19-oic acid, 892 52, 133, 359
15a[2' -methylbutyryloxy]-ent-
Kaur-16-en-19-oic acid, 15{J-angeloyloxy-ent- 658 52, l33, 359
Kaur-16-en-19-oic acid, 15{J-hydroxy-ll-oxo-ent- 673 52, 133, 361
Kaur-16-en-19-oic acid, 15{J-hydroxy-ent- 647 51, l32, 359
Kaur-16-en-19-oic acid, 15{J-senecioyloxy-ent- 660 51, l33, 359
Kaur-16-en-19-oic acid, 15{J-tigloyloxy-ent- 659 51, l33, 359
Kaur-16-en-19-oic acid, 18-angeloyloxy-ent- 643 51, 132,358
Kaur-16-en-19-oic acid, 18-isovaleryloxy-ent- 645 51, l32, 358
Kaur-16-en -19-oic acid, 18-senecioyloxy -en t- 644 51, l32, 358
Kaur-16-en-19-oic acid, 3a-acetoxy-ent- 629 50, l32, 358
Kaur-16-en-19-oic acid, 662 52, l33, 359
3a-angeloyloxy-9{J-hydroxy-ent-
Kaur-16-en-19-oic acid, 3a-angeloyloxy-ent- 630 50, 132, 358
Kaur-16-en-19-oic acid, 663 52, l33, 360
3a-cinnamoyloxy-9{J-hydroxy-ent-
Kaur-16-en-19-oic acid, 3a-cinnamoyloxy-ent- 632 50, l32, 358
Kaur-16-en-19-oic acid, 3a-hydroxy-ent- 628 50, 132, 358
Kaur-16-en-19-oic acid, 3a-isovaleryloxy-ent- 634 51, l32, 358
Kaur-16-en-19-oic acid, 3a-senecioyloxy-ent- 633 51, l32, 358
Kaur-16-en-19-oic acid, 3a-tigloyloxy-ent- 631 50, l32, 358
Kaur-16-en-19-oic acid, 675 52, l34, 360
31', 9{J-dihydroxy-15a-angeloy loxy-ent-
Kaur-16-en-19-oic acid, 676 52, l34, 360
3{J,9{J-dihydroxy-15a-senecioyloxy-ent-
Kaur-16-en-19-oic acid, 677 52, l34, 360
3{J,9{J-dihydroxy-15a-tigloyloxy-ent-
Kaur-16-en-19-oic acid, 869 52, l34, 361
9{J,11{J-dihydroxy-15a-angeloyloxy-ent-
Kaur-16-en-19-oic acid, 664 52, l33, 360
91', 15a-dihydroxy-ent-
[grandifloric acid, 9{J-hydroxy]
Kaur-16-en-19-oic acid, 9{J-hydroxy-15a- 819 52, 133, 360
[3' -hydroxy-2'-methylbutyryloxy]-ent-
Kaur-16-en-19-oic acid, 667 52, l33, 360
9{J-hydroxy-15a-acetoxy-ent-
Kaur-16-en-19-oic acid, 665 52, l33, 360
9{J-hydroxy-15a-angeloyloxy-ent-
Kaur-16-en-19-oic acid, 670 52, l33, 360
9{J-hydroxy-15a-cinnamoyloxy-ent-
Kaur-16-en-19-oic acid, 669 52, l33, 360
9{J-hydroxy-15a-isovaleryloxy-ent-
Kaur-16-en-19-oic acid, 668 52, l33, 360
9{J-hydroxy-15a-senecioyloxy-ent-
Kaur-16-en-19-oic acid, 666 52, l33, 360
9{J-hydroxy-15a-tigloy!oxy-ent-
606 Compound Index

Kaur-16-en-19-oic acid, 636 51, 132,360
9(3, 13(3-dihydroxy-15a-angeloyloxy-
Kaur-16-en-19-oic acid, 3(3-angeloyloxy-ent- 635 51, 132,358
Kaur-16-en-19-oic acid, 7(3-hydroxy-( -)- 1000 51, 132,358
Kaur-16-en-19-oic acid, 17 -carbomethoxy-ent- 812 52, 133, 368
Kaur-16-en-19-oic acid, 943 52, 136,363
9(11)-dehydro-15a-cinnamoyloxy-ent-
Kaur-16-en-3a,19-diol, (-)- 623 50, 132, 358
Kaur-16-ene, 19-hydroxy-ent- 619 50, 131, 357
Kaur-16-ene, 18-nor-ent- 752 56, 139, 372
Kaur-16-ene, 19-acetoxy-ent- 620 50, 131, 357
Kaur-16-ene, 19-nor-ent- 750 56, 140,373
Kaur-16-ene, 19-oxo-ent- 624 50, 132,358
Kaur-16-ene, 4a-hydroxy-19-nor-ent- 751 56, 140,374
[Ruilopeziol]
Kaur-16-ene, 753 56, 139, 372
4(3-hydroxy -18- nor-en t - [4-epi -ruilopeziol]
Kaur-16-ene, ent- 618 50, 131, 357
Kaur-9(11), 15(16)-dien-19-oic acid, 705 54, 134,364
3a- isobutyry loxy -en t-
[3a-isobutyryloxy-polymnia acid]
Kaur-9(11),15(16)-dien-19-oic acid, 704 54, 134, 364
3a- isovalery loxy -en t-
[3a-isovaleryloxy-po1ymnia acid]
Kaur-9( 11), 15(16)-dien-19-oic acid, 706 54, 134,364
3a-tigly1oxy-ent-
[3a-tigly1oxy-po1ymnia acid]
Kaur-9(11),16-dien-19-oic acid, 12-oxo-ent- 695 53, 134, 363
Kaur-9( 11), 16-dien-19-oic acid, 12(3-ethoxy-ent- 998 53, 134, 363
Kaur-9(11), 16-dien-19-oic acid, 12(3-hydroxy-ent- 694 53, 134, 363
Kaur-9( 11), 16-dien-19-oic acid, 15a-hydroxy-ent- 696 53, 134, 363
Kaur-9(11),16-dien-19-oic acid, 2(3-hydroxy-ent- 691 53, 134, 363
Kaur-9(l1),16-dien-19-oic acid, ent- 690 53, 134, 363
Kaur-9(l1 )-en-19-oic acid, 16a, 17 -dihydroxy-ent- 739 55, 136,368
Kauran-16(3-o1, (-)- 1001 54, 135, 366
Kauran-19-al, 16a-hydroxy-ent- 1255 56, 136, 362
Kauran-17,19-dial, 16(3-H-ent- 737 55, 135, 367
Kauran-17,19-dioic acid, 16a( - )- 990 55, 136, 367
Kauran-17,19-dioic acid, 16a-H-ent- 925 55, 135, 367
Kauran-17-al, 16(3-H-ent- 729 55, 135, 367
Kauran-17-al, 740 55, 136, 367
18-[p-hydroxyhydro-cinnamoyloxy] -ent-
Kauran-17-al, 19-hydroxy-16(3-H-ent- 730 55, 135, 367
Kauran-17-oic acid, 16(3-H-ent- 731 55, 135, 367
Kauran-17 -oic acid, 19-hydroxy-16(3-H-ent- 732 55, 135, 367
Kauran-19-a1, 16a,17-epoxy-ent- 735 54, 135, 365
Compound Index 607

Kauran-19-al, 16/J,17-epoxy-ent- 712 54, 135, 365
Kauran-19-al-17-oic acid, 16a( -)- 989 55, 136, 367
Kauran-19-oic acid, 748 56, 136, 368
(16R)-11a-hydroxy-15-oxo-ent-
Kauran-19-oic acid, 747 55, 136, 368
11/J-hydroxy-15-oxo-16a-H-ent-
Kauran-19-oic acid, 746 55, 136, 368
15a, 16a-epoxy-17-hydroxy-ent-
Kauran-19-oic acid, 716 54, 135, 366
15a-acetoxy-16,17-epoxy-ent-
Kauran-19-oic acid, 715 54, 135, 365
15a-angeloyloxy-16,17-epoxy-ent-
[Perymenium acid]
Kauran-19-oic acid, 717 54, 135, 366
15/J-angeloyloxy-16,17-epoxy-ent-
Kauran-19-oic acid, 718 54, 135, 366
15/J-tigloyloxy-16,17-epoxy-ent-
Kauran-19-oic acid, 16a,17-epoxy-ent- 713 54, 135, 365
Kauran-19-oic acid, 16a-hydroxy-ent- 723 55, 135, 362
Kauran-19-oic acid, 16/J, 17 -dihydroxy-ent- 822 55, 135, 366
Kauran-19-oic acid, 16/J,17-epoxy-ent- 714 54, 135, 365
Kauran-19-oic acid, 742 55, 135, 367
17-[n-dodecanoyloxy]-16/J-H-ent-
Kauran-19-oic acid, 744 55, 136, 367
17-[n-hexadecanoyloxy]-I6J3-H-ent-
Kauran-19-oic acid, 745 55, 136, 368
17-[n-octadecanoyloxy]-16/J-H-ent-
Kauran-19-oic acid, 743 55, 136, 367
17-[n-tetra-dodecanoyloxy]-16/J-H-ent-
Kauran-19-oic acid, 17-hydroxy-16a-H-ent- 924 55, 135, 367
Kauran-19-oic acid, 17-hydroxy-16/J-H-ent- 738 55, 135, 367
Kauran-19-oic acid, 741 55, 136, 367
17-isobutyrloyloxy-16/J-H-ent-
Kauran-19-oic acid, 17 -nor-16-oxo-ent- 749 56, 139, 372
Kauran-19-oic acid, 16a, 17 -dihydroxy-ent- 728 55, 135, 362
Kauran-19-ol, 16a,17-epoxy-ent- 734 54, 134, 365
Kaurane, 16a, 17, 19-trihydroxy-ent- 726 55, 135, 362
Kaurane, 727 55, 135, 366
16a, 17-dihydroxy-3-oxo-ent-[Abbeokutone]
Kaurane, 16a, 17-dihydroxy-ent- 725 55, 135, 362
[17-hydroxy-ent-kauranol]
Kaurane, 16a,17-epoxy-ent- 733 54, 134, 365
Kaurane, 736 55, 135, 367
16a-acetyl-19-hydroxy-16-desmethyl-ent-
Kaurane, 16a-hydroxy-19-acetoxy-ent- 722 55, 135, 362
Kaurane, 16a-hydroxy-ent-[( - )-kauranol] 720 54, 135, 362
Kaurane, 16/J, 19-dihydroxy-ent- 852 55, 135, 366
[ent-kauran-16/J,19-diol]
608 Compound Index

Kaurane, 16/3-hydroxy-ent-[ent-kauran-16/3-ol] 851 55, 135, 366
Kaurane, 19-angeloyloxy-16a, 17-epoxy-ent- 710 54, 134, 365
Kaurane, 3a-angeloyloxy-16a, 17-epoxy-ent- 709 54, 134, 365
Kaurane, 3a-angeloyloxy-19-oxo- 711 54, 134, 365
16a, 17-epoxy-ent-
Kaurane, 3/3-acetoxy-16a-hydroxy-ent- 721 54, 135, 362
Kauranol, ent-[( - )-kauranol] 997 50, 131,362
Kauren-16-en-19-oic acid, 656 51, 133,359
15a-[2, 3-epoxy-2-methylbutyloxy ]-ent-
Kauren-16-en-19-oic acid, 15a- 818 52, 133, 359
[2' ,3' -dihydroxy-2-methylbutyryloxy]-
ent-
Kauren-18-oic acid, ent- 926 50, 132, 358
Kauren-19-oic acid, 719 54, 135, 366
12/3-hydroxy-16a, 17-epoxy-16, 17-dihydro-
9(11)-dehydro-ent-
Kauren-19-oic acid, ent- 625 50, 132, 358
Kaurene,4/3,19-epoxy-18-nor-ent- 813 56, 140, 372
Kaurene, 19-[p-hydroxy-hydrocinnamoyloxy]-ent- 622 50, 131,358
Kaurene, 19-formyloxy-methylenoxy-ent- 621 50, 131,357
Kingidiol [Barticulidiol] 846 41, 115,328
Kingidiol, 19-0-malonyl- 1231 45, 118, 328
Kirenol 589 48, 126, 351
Koanoadmantic acid 19 8, 62, 223
Koanolabda-12E,14-diene, seco- 219 20, 82, 259
Koanophyllic acid A 233 21, 86, 263
Koanophyllic acid B 232 21,86,263
Koanophyllic acid C 234 21, 86,263
Koanophyllic acid D 235 22,86,264
Kolav-13(16),14-diene, 3a,4a, 15, 16-diepoxy- 1076 44, 117,336
Kolav-13-en-15-oic acid lactone, 1082 44, 118, 338
16,3a,4/3-trihydroxy
Kolav-13-en-15-oic acid lactone, 1081 44, 117,338
16-hydroxy-3-oxo-
Kolav-13-en-15-oic acid lactone, 1080 44, 117,338
16-hydroxy-3a,4a-epoxy-
Kolav-13E-en-15-al, 3-oxo- 1079 44, 117,337
Kolav-13E-en-15-al, 3a,4a-epoxy- 1077 44, 117,337
Kolav-13Z-en-15-al, 3-oxo- 1078 44, 117,337
Kolav-13Z-en-15-al, 3a,4a-epoxy- 1075 44, 117,337
Kolav-3, 13(16), 14-trien-18-oic acid, 513 41, 115,329
2/3-hydroxy-15,16-epoxy-ent-
15, 16-epoxy-ent-[Junceic acid]
15,16-epoxy-19-hydroxy-ent-
[Hautriwaic acid]
Ko1av-3, 13(16), 14-trien-18-oic acid, 519 41, 115, 329
15, 16-epoxy-2a, 19-dihydroxy-ent-
Compound Index 609

Kolav-3, 13(16), 14-triene, 15,16-epoxy- 507 41, 115,328
Kolav-3-en-15-oic acid lactone, 16,16-dihydroxy- 565 43, 117,333
Kolav-3-en-15-oic acid, 13,14-dihydro- 503 41, 115,325
Kolav-3-en-15-oic acid, 16-oxo- 542 43, 116,331
Kolav-3-en-15-oic acid, 18-acetoxy- 504 41, 115,325
Kolav-3-en-15-ol, 6a,18-dihydroxy-17-acetoxy- 488 40, 114, 325
Kolav-3-en-15-ol, 489 40, 114, 325
6a,18-dihydroxy-17-phenylacetoxy-
Kolav-3-en-15-ol, 491 40, 114, 325
6a-hydroxy-17-acetoxy-18-oxo-
Kolav-3-en-15-ol, 490 40, 114, 325
6a-hydroxy-17-phenylacetoxy-18-oxo-
Kolav-3-ene, 569 44,117,335
18-malonyloxy-15-hydroxy-15,16-epoxy-
Kolava-3,13E-dien-15-oic acid, 16-hydroxy- 865 42, 116,331
Kolava-3,13Z-dien-15-oic acid lactone, 864 43, 116, 332
16,16-dihydroxy-
Kolavan-2-on-15-oic acid, 3{3,4{3-epoxy- 506 41, 115,328
Kolavelool [Kolavenool] 479 40, 114, 324
Kolavelool, 6{3-angeloyloxy- 480 40, 114, 324
[6{3-Angeloyloxy-kolavenool]
Kolaven-15, 18-dioic acid dilactone, 563 43, 117,333
16, 19-dihydroxy-13, 14-dihydro-
Kolaven-15,18-dioic acid dilactone, 561 43, 116, 333
7-oxo-16,19-dihydroxy-13,14-dihydro-
Kolaven-15,18-dioic acid dilactone, 559 43, 116, 332
7a, 16, 19-trihydroxy-
Kolaven-15,18-dioic acid dilactone, 562 43,117,333
7 a, 16, 19-trihydroxy-13, 14-dihydro-
Kolaven-15-al, 17 -hydroxy-13, 14-dihydro- 492 40, 114, 325
Kolaven-15-al, 17-hydroxy-13E- 535 42, 116, 323
Kolaven-15-al, 17-hydroxy-13Z- 534 42, 116, 326
Kolaven-15-oic acid lactone, 564 43, 117,333
16-hydroxy-13,14-dihydro-
Kolaven-15-oic acid lactone, 963 43, 117,333
16-hydroxy-16-methoxy-18-acetoxy-
Kolaven-16-oic acid lactone, 15-hydroxy-2-oxo- 568 44, 117,335
Kolaven-16-oic acid lactone, 2{3,15-dihydroxy- 567 44, 117,334
Kolavenic acid lactone, 16,18-dihydroxy- 550 43, 116, 332
Kolavenic acid lactone, 556 23, 88, 266
16-hydroxy-3,4-epoxy-[Structure was revised
to 5a, lOa-cis-]
Kolavenic acid lactone, 2a,16-dihydroxy- 544 43, 116, 332
Kolavenic acid lactone, 557 23, 88, 266
7{3-angeloyloxy-16-hydroxy-3 ,4-epoxy-
[Revised to 5a, lOa-cis-]
Kolavenic acid, 16-18-dihydroxy- 538 42, 116,331
Kolavenic acid, 16-acetoxy-18-hydroxy- 539 42, 116, 331
Kolavenic acid, 16-acetoxy-18-oxo- 541 43, 116, 331
610 Compound Index

Kolavenic acid, 16-hydroxy-18-oxo- 540 43, 116,331
Kolavenic acid, 2-oxo- 961 41, 115,327
Kolavenic acid, 6-angeloyloxy- 498 40, 114, 323
[6a-Angeloyloxy-13,14E-kolavenoic acid]
Kolavenic acid, 6-tigloyloxy- 499 40, 114, 323
[6a- Tigloy loxy -13, 14 E-kolavenoic acid]
Kolavenic acid, 6a, 7{3-diacetoxy-13Z- 1029 44, 117,336
Kolavenic acid, 6a, 7{3-dihydroxy-2-oxo-13E- 1030 44, 117,336
Kolavenic acid, 6a,7{3-dihydroxy-nor- 1032 46, 123, 346
Kolavenic acid, 6a-angeloyloxy-7{3-acetoxy-13Z- 1028 44, 117,336
Kolavenic acid, 6a-isobutyryloxy- 1027 44, 117,335
7(3-acetoxy-13-Z-
Kolavenic acid, 6a-isobutyryloxy- 1031 44, 117,336
7{3-angeloyloxy-13,14-dihydro-
Kolavenic-15-acid lactone, 551 23, 43, 265
2a,16-dihydroxy-3a,4a-epoxy-
Kolavenic-15-acid lactone, 552 23, 43, 265
6{3-angeloyloxy-16-hydroxy-3a ,4a-epoxy-
Kolavenoic acid [13, 14E-Kolavenoic acid] 495 40, 114, 323
Kolavenoic acid, 13,14Z- 493 40, 114, 326
Kolavenoic acid, 2{3-acetoxy-13, 14Z- 494 40, 114,326
Kolavenoic acid, 6-acetoxy- 496 40, 114,323
[6{3-Acetoxy-13, 14E-kolavenoic acid]
Kolavenoic acid, 6-angeloyloxy- 497 40, 114, 323
[6{3-Angeloyloxy-13, 14E-kolavenoic acid]
Kolavenoic acid, 6a,18-dihydroxy-17-acetoxy- 501 40, 115, 327
Kolavenoic acid, 502 40, 115, 327
6a,18-dihydroxy-17-phenylacetoxy-
Kolavenol 475 39, 114, 322
Kolavenol acetate, 16-hydroxy-2a-acetoxy- 1228 45, 118, 324
3{3,4{3-epoxy-3,4-dihydro-
Kolavenol acetate, 2a,16-dihydroxy- 478 39, 114, 324
3{3 ,4{3-epoxy-3 ,4-dihydro-
Kolavenol acetate, 477 39, 114, 324
2a-hydroxy-3{3 ,4{3-epoxy-3 ,4-dihydro-
Kolavenol arachidate, 17 -hydroxy-13, 14-dihydro- 482 40, 114, 325
Kolavenol arachidate, 17-hydroxy-13E- 1010 40, 114,322
Kolavenol behenate, 17-hydroxy-13,14-dihydro- 483 40, 114, 325
Kolavenol behenate, 17-hydroxy-13E- 1011 40, 114, 322
Kolavenol, 17-hydroxy-13, 14-dihydro- 481 40, 114,325
Kolavenol, 17-hydroxy-13E- 476 39, 114,322
Kolavenol, 17-oxo-13, 14-dihydro- 486 40, 114,325
Kolavenol, 18-succinyloxy-13,14-dihydro- 484 40, 114,325
Kolavenol, 485 40, 114,326
2a-hydroxy-3a,4a-epoxy-13,14-dihydro-
Kolavenool, 6{3-acetoxy-2-oxo- 1025 23,88,268
Labda-8(17), 12E, 14-triene, 434 33, 100,305
18, 19-dihydroxy-ent-
Compound Index 611

Labda-13(14)E-en-15-al,8-hydroxy-ent- 349 29,96,289
Labda-13( 14)E-en-15-o1, 8-hydroxy -ent- 348 29, 96, 289
Labda-13( 14)Z-en-15-al, 8-hydroxy -ent- 350 29,96,290
Labda-13(16),14-diene, 3a-angeloyloxy- 416 32,99,302
8-hydroxy-15, 16-epoxy-ent-
Labda-13( 16), 14-diene, 8a-hydroxy -ent- 441 33, 100
Labda-13-Z-en-15-oic acid, 460 34, 100,308
6, 16-dioxo-8, 12-oxido-ent-
Labda-13-en-15-oic acid, 3, 17-dioxo-8/3-H-ent- 341 29, 96, 288
Labda-13E-en-15, 17-dioic acid, 3/3-H-ent- 345 29,96,288
Labda-13Z-en-15,17-dioic acid, 8/3-H-ent- 344 29, 96, 288
Labda-I3Z-en-15-oic acid, 3,17-dioxo-8a-H-ent- 342 29, 96, 288
Labda-13Z-en-15-oic acid, 3-oxo-8,17-epoxy-ent- 346 29, 96, 289
Labda-I3Z-en-15-oic acid, 1201 37, 108,316
8-oxo-8-desmethyl-ent-
Labda-13Z-en-15-oic acid, 3,8-dioxo-ent- 1202 37, 108,316
Labda-13Z-en-15-oic acid, 3a, 343 29, 96, 288
8a-dihydroxy-17-oxo-8/3-H-ent-
Labda-13Z-en-15-oic acid, 340 29, 96, 288
3a-hydroxy -17 -oxo-8a-H -ent-
Labda-I3Z-en-15-oic acid, 339 29, 96, 288
3a-hydroxy-17-oxo-8/3-H-ent-
Labda-7, 13(16), 14-trien-15, 16-epoxy-18-oic acid, 415 32, 99, 302
5/3,9/3H,lOa-ent-
Labda-7, 13(16), 14-trien-2/3,3a-diol, 1188 36, 102,310
15, 16-epoxy-ent-
Labda-6,13-diene, 15,16, 17-triacetoxy-ent- 364 30,97,294
Labda-6,13-diene, 15,16-diacetoxy-ent- 363 30,97,293
Labda-6, 13E-dien-15, 17-dioic acid, 381 30,98,296
16-acetoxy-ent-
Labda-6, 13E-dien-15-oic acid, 380 30,98,296
16-acetoxy-17-oxo-ent-
Labda-6, 13E-dien-15-oic acid, 466 37, 108,316
16-acetoxy -8-oxo-8-desmethyl-ent-
Labda-6,13E-dien-15-oic acid, 465 37, 108,315
16-acetoxy-8/3-formyl-8-desmethy l-ent-
Labda-6,13E-dien-15-oic acid, 379 30,98,296
8a,16-dihydroxy-ent-
Labda-6, 8( 17), 13-trien-15-oic acid lactone, 384 31,98,297
16-hydroxy-ent-
Labda-6,8(17), 13-trien-15-oic acid, 365 30, 97, 294
16-hydroxy-ent-
Labda-6,8(17), 13-dien-15-oic acid, ent- 356 29,97,291
Labda-7(8),13E-diene, 15,16, 17-trihydroxy-ent- 362 30, 97, 293
Labda-8(17),13-diene, 7/3,15, 16-trihydroxy-ent- 382 30, 98, 296
Labda-7, 13-dien-2/3, 15-diol, 1192 36, 102, 311
3a-angeloyloxy-ent-
Labda-7,13E-diene, 2/3 ,3{3, 15-trihydroxy-ent- 1193 36, 102, 311
612 Compound Index

Labda-7,13-dien-15-oic acid lactone, 387 31, 98, 298
12,16-dihydroxy-ent-
16,12,16-trihydroxy-ent-
Labda-7, 13-dien-15-oic acid lactone, 391 31, 98, 298
16,12,160:-trihydroxy-ent-
Labda-7, 13-dien-15-oic acid lactone, 392 31,98,298
16, 12, 16~-trihydroxy-ent-
16,16-dihydroxy-6-oxo-ent-
16,160:-dihydroxy-ent-
Labda-7,13-dien-15-oic acid lactone, 395 31,98,298
16,160:-dihydroxy-17-oxo-ent-
[Acritolongifolide A]
16, 16~-dihydroxy-ent-
16, 16~-dihydroxy-17-oxo-ent-
[Acritolongifolide B]
16-hydroxy-ent-
16-hydroxy-6-oxo-ent-
Labda-7,13-dien-15-oic acid, 371 30,97,295
Labda-7,13-dien-15-oic acid, 1180 36, lO2, 294
16-hydroxy-17-methoxy-ent-
Labda-7, 13-dien-15-oic acid, 355 29,97,290
2~-angeloy1oxy-ent-[Dendroidinic acid]
15,12,150:-trihydroxy-ent-
15, 12, 15~-trihydroxy-ent-
15-hydroxy-ent-
Labda-7,13-diene, 353 29,97,290
30:,15-diacetoxy-l1-hydroxy-ent-
Labda-7,13E-dien-15-oic acid, ent- 354 29,97,291
Labda-7,13E-dien-15-oic acid, 367 30, 97, 294
Labda-7,13E-dien-15-oic acid, 377 30,98,295
16-acetoxy-60:-hydroxy-17-oxo-ent-
16-acetoxy-6~-hydroxy-17-oxo-ent-
Labda-7,13E-dien-15-oic acid, 16-hydroxy-ent- 366 30,97,294
Compound Index 613

Labda-7, 13E-dien-15-oic acid, 378 30, 98, 295
16-methoxy -6-oxo-en t-
17-hydroxy-16-acetoxy-ent-
Labda-7,13Z-dien-15-oic acid, 368 30,97,294
Labda-7, 13Z-dien-15-oic acid, 374 30,97,295
Labda-7,13Z-dien-15-oic acid, 6,16-dioxo-ent- 375 30, 97, 295
Labda-7,14-diene, 13-hydroxy-ent- 447 34, 100, 307
Labda-7,14-diene, 13-hydroxy-3-oxo-ent- 449 34, 100, 308
Labda-7,14-diene, 3, 13-dihydroxy-ent- 448 34, 100, 307
Labda-7,13(Z)-dien-6-one, 15-hydroxy-ent- 352 29,96,290
Labda-7, 13 (Z)-diene-6{3 , 15-dihydroxy-ent- 351 29,96,290
Labda-7 -en-15-oic acid, 361 30,97,292
2{3-angeloylocy-ent-
[13, 14-Dihydro-dendroidinic acid]
Labda-7-en-aldehyde, 471 38, 109,317
nor-ent-[13 , 14, 15, 16-Tetra-nor-
2-oxo-ent-labda-7-ene]
Labda-8(17), 12E, 14-triene, 18-hydroxy-ent- 433 33, 100, 305
Labda-8(17), 12E, 14-triene, 19-hydroxy-ent- 431 33, 100, 305
Labda-8(17), 12E, 14-triene, 3cx,19-dihydroxy-ent- 432 33, 100, 305
Labda-8(17), 12E, 14-triene, 18,19-diacetoxy-ent- 1185 36, 102, 305
Labda-8(17), 12E-diene, 14-oxo-15-nor-ent- 469 38, 108, 316
Labda-8(17), 13Z-diene, 1191 36, 102,311
2{1, 15, 16, 18-tetrahydroxy-
3cx-angeloyloxy-ent-
Labda-8(17), 13(14 )-dien-16-oic acid lactone, 397 31,98,299
7{3,15-dihydroxy-ent-
Labda-8(17), 13, 14E-dien-15-ol, 7(3-acetoxy-ent- 328 28, 96, 285
Labda-8(17), 13E-dien-15-oic acid, 1189 36, 102,310
3cx,18-dihydroxy-ent-
Labda-8( 17), 13E-dien-15-oic acid, 1190 36, 102, 311
3cx-angeloyloxy-18-hydroxy-ent-
Labda-8( 17), 327 28, 96, 284
13-dien-15-0-bernsteinoate, ent-
Labda-8(17),13-dien-15-0-bernsteinoate, 347 29, 96, 289
8, 17-dihydro-8{3, 17-epoxy-ent-
Labda-8(17), 13-dien-15, 16-o1ide, 1181 36, 102, 297
2{3,18-dihydroxy-ent-
Labda-8(17),13-dien-15, 16-olide, 1182 36, 102, 297
3{3-angeloyloxy-18-hydroxy-ent-
Labda-8(17),13-dien-15, 16-o1ide, 1183 36, 102, 297
3{3-ange1oy1oxy-18{3-g1ucopyranosy1oxy-ent-
Labda-8(17), 13-dien-15, 16-olide, 1184 36, 102,297
614 Compound Index

3a-angeloyloxy-2fj,18-dihydroxy-ent-
Labda-8(17),13-dien-15-oic acid lactone, 385 31,98,297
Labda-8(l7),13-dien-15-ol, ent- 326 28,96,284
Labda-8(17),13-dien-15-o1, 2-oxo-ent- 849 28, 96, 286
Labda-8(l7), 13-dien-15-o1, 2a-hydroxy-ent- 848 28,96,285
Labda-8(l7),13E-dien-15-acetoxy-18-oic 330 28, 96, 285
acid,ent-[Viscidic acid B]
Labda-8(17),13E-dien-15-al, 2-oxo-ent- 333 28, 96, 286
Labda-8(l7), 13E-dien-15-al, 2a-hydroxy-ent- 331 28,96,285
Labda-8(17), 13E-dien-15-oic acid, 335 28,96,285
ent-[E-Copalic acid]
Labda-8(l7), 13E-dien-15-o1-18-oic acid, 329 28,96,285
ent-[Viscidic acid A]
Labda-8(l7), 13E-diene, 844 28,96,285
3a-angeloyloxy-15, 18-dihydroxy-ent-
Labda-8(l7), 13Z-dien-15-al, 2-oxo-ent- 334 28,96,287
Labda-8(l7), 13Z-dien-15-al, 2a-hydroxy-ent- 332 28,96,287
Labda-8(17), 13Z-dien-15-oic acid, 336 28,96,287
ent-[Z-Copalic acid]
Labda-8(l7),13Z-dien-15-oic acid, 338 28,96,287
3a,7a-dihydroxy-ent-
Labda-8(17),13Z-dien-15-oic acid, 337 28,96,287
3a-hydroxy-ent-
Labda-8(17), 14-dien-18-oic acid, 439 33, 104,306
12a, 13aE-epoxy-ent-
Labda-8(17), 14-dien-18-oic acid, 437 33, 104, 306
12a, 13aZ-epoxy-ent-
Labda-8(17), 14-dien-18-oic acid, 440 33, 105, 306
12fj,13fjE-epoxy-ent-
[12, 13-Dehydro-12, 13a-epoxy-ozic acid]
Labda-8(l7) , 14Z-dien-18-oic acid, 438 33, 104, 306
12fj,13fjZ-epoxy-ent-
Labda-8(17)-en-15-oic acid, 16-oxo-ent- 383 30,98,296
Labda-8(l7)-en-15-oic acid, 2-oxo-ent- 861 30,97,292
Labda-8(l7)-en-15-oic acid, 860 29, 97, 292
2a-[2-methylbutyryloxy]-ent-
Labda-8(17)-en-15-oic acid, 858 29,97,292
2a-angeloyloxy-ent-
Labda-8(17)-en-15-oic acid, 2a-hydroxy-ent- 857 29,97,291
Labda-8(l7)-en-15-oic acid, 2a-tigloyloxy-ent- 859 29,97,292
Labda-8(l7)-en-15-o1, 2-oxo-ent- 359 30,97,292
Labda-8(l7)-ene, 13-oxo-14,15-bis-nor-ent- 470 38, 108,317
Labda-8( 17)-ene, 975 32,99300
18-angeloyloxy-3a-hydroxy-13-furyl-ent-
Labda-8(l7)-ene, 2a,15-dihydroxy-ent- 357 29,97,291
Labda-8(l7)-ene, 974 32,99300
3a-angeloyloxy-18-hydroxy-13-furyl-ent-
Compound Index 615

Labdan-15-oic acid, 863 30,97, 292
2a-[2-methylbutyryloxy ]-8(J, 17-epoxy-ent-
Labdan-15-oic acid, 862 30,97,292
2a-angeloyloxy-8(J,17-epoxy-ent-
Labdane triol la, 18-nor-ent- 828 38, 110,318
Labdane triol 2a,18-nor-ent- 829 38, 110, 318
Labdaturbinic acid, friedo- 1211 38, 110,319
Labd-1 (10), 13E-dien-15-ol, 2-oxo-ent-friedo- 1209 38, 110,319
Labd-1(1O),13E-diene, 2a,15-dihydroxy- 1210 38, 110,319
ent-friedo-
Labd-7-ene,2(J,3(J,15-trihydroxy- 1197 36, 102, 311
Labd-7-en-2-0-[fuco-pyranoside-4' -O-acetate], 1203 38, 109,317
14,15-nor-ent-
Labd-7-en-15-oic acid, 4(J-hydroxymethyl- 1145 17,75,244
Labd-(8,9)-ene, 13R, 14R, 15-trihydroxy- 87 13,71,237
Labd-13-ene, 8a,15-dihydroxy- 1103 12,71,239
Labd-14-en-18-oic acid, 7-oxo-9(J' 13(J-epoxy-ent- 1019 34, 101, 309
Labd-14-ene, 1017 34, 101, 309
18-hydroxy-7-oxo-9(J,13(J-epoxy-ent-
Labd-14-ene, 7, 18-dioxo-9(J' 13(J-epoxy-ent- 1018 34, 101, 309
Labd-7-en-15-oic acid, 2-hydroxy-17-methoxy- 1179 35, 102,293
Labd-7 -en-15-oic acid, 3(J-hydroxy- 1146 75, 244
[= 120]
Labd-7-en-15-oic acid, 870 15, 73, 244
3(J-hydroxy-2a-senecioyloxy-13-
Labd-7-en-2a, 15-diol, 13- 871 14, 73, 244
Labd-7-ene, 13R, 14R, 15-trihydroxy- 86 13,71,237
Labd-7-ene, 994 13, 71, 245
15-[2-methy lbutyry loy loxy ]-3a- hydroxy-
Labd-7-ene, 2a-hydroxy-15- 872 14, 73, 244
[3 ,4-dihydroxy-cinnamoyloxy]-13-
[4-hydroxy-3-methoxy-cinnamoyloxy]-13-
[4-hydroxy-cinnamoyloxy]-13-
Labd-7-ene, 3a,15-dihydroxy- 993 13,71,245
Labd-7-13E-dien-2-0-iJ-fucopyranoside, 1165 35, 102, 285
3a-angeloyloxy-2iJ,15-dihydroxy-ent-
Labd-7,13E-dien-2-0-(J- 1166 35, 102,285
[fucopyranoside-4' -O-acetate],
3a-angeloyloxy-2iJ,15-dihydroxy-ent-
Labd-7,13E-dien-2-0-(J- 1167 35, 102, 285
[fucopyranoside-3 ' -O-acetate],
3a-angeloyloxy-2(J,15-dihydroxy-ent-
Labd-7,13E-dien-2-0-(J- 1168 35, 103, 285
[fucopyranoside-4 ' -O-acetate],
3a-angeloyloxy-2iJ, 15, 15-trihydroxy-ent-
Labd-7,13(l6)-dien-2-0-iJ- 1169 35, 103, 285
616 Compound Index

[fucopyranoside-4 -O-acetate],
I
3a-angeloyloxy-2,8, 14, 15-trihydroxy-ent-

Labd-7,13E-dien-2-0- 1170 35, 103, 286
[rhamnopyranoside-4 -O-acetate],
I
3a-angeloy loxy-2,8, 15-dihydroxy-ent-

Labd-7,13E-dien-2-0-,8-xylopyranoside, 1171 35, 103, 286
3a-angeloy loxy-2,8, 15-dihydroxy-ent-
Labd-13E-ene, 2,8,8,8,15-trihydroxy-ent- 1174 35, 101,289
Labd-13E-en-8-0-,8-xy lopyranoside, 1172 35, 103, 286
8,8,15-dihydroxy-ent-
Labd-8(l7)-en-15-al-19-oic acid 977 15, 73, 242
Labd-8(l7)-en-15-oic acid, 2,8-acetoxy- 959 15, 73, 241
Labd-8(17)-ene, 13,14, 15-trihydroxy- 89 13,71,240
Labd-8(17)-ene, 14,15-dihydroxy- 88 13, 71, 240
Labd-8(l7)-ene, 14-acetoxy-15-hydroxy- 92 13,72,240
Labd-8(l7)-ene, 15-acetoxy-13,14-dihydroxy- 91 13,72,240
14-propionyloxy-
Labd-8(17)-ene, 15-hydroxy-13, 14-epoxy- 85 13,71,240
Labd-8(l7)-ene, 3a, 7a, 15-trihydroxy- 995 13,71,241
Labd-8(l7)-en-19-oic acid, 15-hydroxy-ent- 1173 35, 101,287
Labd-8,14-diene, 13,18-dihydroxy-7-oxo-ent- 1016 34, 101, 309
Labd-8(17), 12E, 14-trien-19-oic acid 1104,1147 17,75,245
Labda-12(E), 14-diene, 9a,19-dihydroxy- 152 16, 74, 247
Labda-13E-en-15-oic acid, 5(3,8(3-peroxy-ent- 1044 35, 101,312
Labda-5, 13E-dien-15-oic acid, 18-hydroxy- 1059 38, 110,319
10-desmenthyl-9a-methyl-8,8(H)-ent-
Labda-7 (8), 13E-dien-15, 18-dioic acid, 1043 34, 101,312
6,8-isovaleryloxy-ent-
6,8-hydroxy-18-oxo-ent-
Labda-7(8), 13E-diene, 15,18-diacetoxy- 1012 34, 101,309
2,8-hydroxy-ent-[ or enantiomer]
Labda -7 (8), 13 E-diene, 18-acetoxy- 1013 34, 101, 309
2,8, 15-dihydroxy-ent-[or enantiomer]
Labda-7,13-dien-15-acid-16-1actone, 17-hydroxy- 965 19,81,257
Labda-7,13-dien-15-acid-16-1actone, 17-oxo- 966 20,81,257
Labda-7,13E-dien-15-oic acid, 2a-tigloyloxy- 112 14, 72, 242
Labda-7, 13E-dien-15-oic acid, 3-oxo- 117 14, 72,243
Labda-7, 13E-dien-15-oic acid, 1045 35, 101,312
6,8,18-dihydroxy-ent-
Labda-7, 13Z-15-oic acid, 3a-hydroxy- 116 13, 72, 241
Labda-7-en-15,17-dioic acid, ent- 1052 35, 101,293
Labda-7-en-15-oic acid, 17-acetoxy-ent- 1047 35, 101,293
Labda-7-en-15-oic acid, 17-hydroxy- 1046 35, 101,293
Labda-7-en-15-oic acid, 17-oxo-ent- 1048 35, 101,293
Compound Index 617

Labda-7-en-15-oic acid, 1053 35, 101, 293
19-hydroxy-17-acetoxy-ent-
Labda-7-en-15-oic acid, 2a,17-dihydroxy-ent- 1049 35, 101, 293
Labda-7-en-15-oic acid, 2a-hydroxy-17- 1050 35, 101, 293
acetoxy-ent-
Labda-7-en-15-oic acid, 2a-hydroxy-17-oxo-ent- 1051 35, 101,293
Labda-7-en-15-oic acid, 3a-hydroxy- 119 14, 72, 243
Labda-7-en-15-oic acid, 3/3-hydroxy- 120 14, 73, 243
Labda-8(17), 13(16), 14-triene, 18-hydroxy- 1037 34, 101,310
3a-angeloyloxy-15, 16-epoxy ,ent-
Labda-8(17), 13(16), 14-triene, 2/3,18-dihydroxy- 1038 34, 101, 310
3a-angeloyloxy-15, 16-epoxy ,ent-
Labda-8(17),13-diene 78 12, 71, 239
Labda-8(17), 13E-dien-15-oic acid 111 14, 72, 238
18-hydroxy-ent-
Labda-8(17), 13E-dien-15-oic acid, 1040 34, 101
ent-[E-Copalic acid]
Labda-8(17),13E-diene, 1014 34, 101,285
3a-acetoxy-15-hydroxy-18-tigloy1oxy-ent-
[or enantiomer]
Labda-8(17), 13E-dien-15, 18-dioic acid, 1164 35, 101,285
ent-[Guamaic acid]
Labda-8(17), 13Z-diene, 1039 34, 101
2/3,15,16,18-tetrahydroxy-3a-angeloyloxy-ent-
Labda-8(l7)-13-dien-15-o1 76 12,71,238
Labda-[7 . 13E-dien]-15-oic acid, 3a-hydroxy- 114 14, 72, 242
Labda-[7 . 13E-dien]-15-oic acid, 3/3-hydroxy- 115 14, 72, 242
Labdan-15-oic acid, 8a-hydroxy- 958 14, 70, 237
Labdan-8a, 15-diol 79 13, 70, 237
Labdan-8a,15-diol, 13-epi- 81 13, 70, 237
Labdan-8a,15-diol, 13/3H- 1139 17,70,238
Labdanol acid 121 14, 73, 244
Labden-13-one, 14,15-bisnor-8-hydroxy-11E- 1155 21,85,262
Labdenol acid, (13Z)- 1024 17,74,243
Lambertianic acid, 17-hydroxyiso- 159 16, 74, 250
Lambertianic acid, 7a-hydroxy- 163 16, 74, 250
Ligantrol 74 12, 70, 236
Ligantrol-monoacetate 75 12, 70, 236
Lycaconitine, methyl- 801 59, 148, 383
Lycoctonine [royline; roylenej 802 59, 148, 384
Lycoctonine, anthranoyl- 803 59, 148, 384
Manool, (+)- 996 16, 74, 248
Manool, ent- 442 33, 100, 307
Manool, iso- 1105 16, 74, 248
Manool, 2-oxo-ent- 446 34, 100, 307
Manool, 2a-hydroxy-ent- 444 34, 100, 307
618 Compound Index

Manool, 2,8-hydroxy-ent- 443 34, 100, 307
Manool, 2,8-succinyloxy-ent- 445 34, 100,307
Manool, 3,8-hydroxy-iso- 1106 16, 74, 248
Manool, 3-oxo-iso- 1107 16, 74, 249
Manoyl oxide 272 18, 79, 255
Manoyl oxide, 13-epi- 273 19, 79, 255
Manoyl oxide, ent- 458 37, 107,315
Manoyl oxide, 13-epi-ent- 451 37, 106,314
[ent-8,13,8-Epoxy-14-1abdene]
Manoyl oxide, 3a-acetoxy-ent- 1198 37, 107,314
Manoyl oxide, 19-cinnamoyloxy-3a-hydroxy-ent- 1199 37, 107,314
Manoyl oxide, 3a,19-dihydroxy-ent- 1200 107,314
Manoyl oxide, 19-hydroxy-13-epi-ent- 455 37, 107,314
Manoyl oxide, 2-oxo-13-epi-ent- 454 37, 107,314
Manoyl oxide, 2-oxo-19-hydroxy-13-epi-ent- 456 37, 107,314
Manoyl oxide, 3-oxo-13-epi-ent- 453 37, 107,314
[ent-8, 13,8-epoxy-14-1abden-3-one]
Manoyl oxide, 3a-hydroxy-ent- 452 37, 107,314
Manoyl oxide, 3,8-hydroxy-ent- 459 37, 107,315
Manoyl oxide, 15-oxo-14,15-dihydro- 964 19, 79, 255
Manoyl oxide, 18-benzoyloxy-3,8-hydroxy- 201 19, 79, 255
[18-benzoy l-oxy larcardenasol]
Manoyl oxide, 18-hydroxy-13-epi- 202 19, 79, 255
Manoyl oxide, 200 19, 79, 255
3,8-hydroxy-[18-deoxy-lazarcardenasol]
Melcantho1ide, 1,6, 7-trihydroxy-17-acetoxy- 1006 11,67,231
Melfusanolide, 1,10, 17-trihydroxy- 45 10, 65, 228
Melfusanolide, 1, 10-dihydroxy-17 -acetoxy- 44 10,65,228
Mikanifuran 58 11,67,231
Missourienol A [initially isolated as dehydration 611 49, 129, 355
product: 3-oxo-abieta-7, 13-diene]
Missourienol B [initially isolated as dehydration 612 49, 129, 356
product: 3,8-hydroxy-abieta-7, 13-diene]
Missourienol C [initially isolated as dehydration 613 49, 129, 356
product: 2,8-acetoxy-abieta-7, 13-diene]
Montanol 57 10,66,230
Neophytadiene 59 9,64,226
Nidoanomalin 781 57, 143,377
Nidorella lactone 214 20,81,258
Nidorella lactone, seco- 225 21, 84, 261
Nidorella lactone-6-0-[2-methylbutyrate], seco- 228 21, 84,261
Nidorella lactone-6-0-angelate, 230 21,84,261
5-deoxy-5-hydroxy-5H-seco-
Nidorella lactone-6-0-angelate, seco- 226 21,84,261
Nidorella lactone-6-0-isobutyrate, seco- 227 21,84,261
Nidorella lactone-6-0-isovalerate, seco- 229 21,84,261
Nidorellalactone 254 22, 87, 266
Nidorellalactone, iso- 253 22, 87, 265
Compound Index 619

Nidorellol 141 15, 73, 246
Nidorellol, 6a-angeloyloxy- 143 15, 73, 246
Nidorellol, 6a-hydroxy- 142 15, 73, 246
Nidoreseda acid methyl ester, seco- 256 22, 87, 264
Nidoreseda acid, seco-[Conyzic acid, strictic acid] 255 22, 87, 264
Nidoresedaic acid, 19-acetoxyseco- 912 46, 122, 345
Nivenolide 843 31, 98, 299
Olearin 560 43, 116, 332
Osteomuricone, 1/1,2a-dihydroxy- 311 26,92,278
Osteomuricone, 1/1 ,2a-dihydroxy-15, 16-dihydro- 312 26,92,278
Osteomuricone, 2a-hydroxy- 310 26, 92, 278
Ozic acid, 12,13E- 425 33, 100, 304
[ent-Labda-8(l7), 12E, 14-trien-18-oic acid]
Ozic acid, 2-oxo-12,13Z- 427 33, 100, 304
Ozic acid, 2a-hydroxy-12,13Z- 426 33, 100, 303
Ozic acid, cis- 424 33, 100, 303
Ozic acid, 1/1-acetoxy-trans- 435 33, 100, 305
[l/1-acetoxy-ent-
Labda-8(17), 12E, 14-trien-19-oic acid]
Palarosan, 3a-hydroxy-13-epi- 304 26, 91, 276
Palarosan, 9a-hydroxy-13-epi- 305 26,91,276
Palarosane, 3-oxo- 315 27,93,279
Palarosane, 3/1,18-dihydroxy-[Jesromotetrol] 314 26,93,278
Palarosane, 3a-hydroxy- 306 26, 93, 276
Palarosane, 3/1-hydroxy- 313 26, 93, 278
Paniculoside I 895 53, 138, 370
Paniculoside II 896 53, 138, 370
Paniculoside III 897 53, 138, 370
Paniculoside IV 898 53, 138, 370
Paniculoside V 899 53, 138, 371
Pimar-15-en-8/1-ol, 13-epi- 891 26,92,277
Pimar-9( 11 )-en-19-oic acid, 824 49, 128, 354
ent-8(R),15(S)-epoxy-12a-acetoxy
Pimar-9,1l(15)-dien-19-oic acid, (-)- 600 48, 127, 352
Pimar-9, II (15)-dien-19-ol, (-)- 599 48, 127, 352
Pimara-12a,16-diol, 8, 15R-epoxy-3-oxo-ent- 598 49, 127,353
Pimara-3/1, 12a, 16-triol C-15 epimer lOa, 597 48, 128, 353
8-15-epoxy-ent-
Pimara-3/1, 12a, 16-triol C-15-epimer 9a, 596 48, 127,353
8,15-epoxy-ent-
Pimara-7, 15-dien-19-oic acid, ent- 820 48, 126,351
Pimara-8(l4), 15-dien-19-oic acid, ent- 590 48, 126,351
Pimara-8( 14 )-en-6/1-0-glucoside, 593 48, 126, 353
15/1, 16-dihydroxy-
Pimara-8(l4)-ene, 2/1,15/1,16, 19-trihydroxy- 595 48, 126, 351
Pimara-8(l4)-ene, 6/1,15/1, 16-trihydroxy- 594 48, 126, 353
Pimara-8(l4)-ene, 6/1,15,16, 18-tetrahydroxy-ent- 944 48, 126, 353
Pimaradiene-3/1,18-diol, ent-8(l4), 15- 1248 48, 126,351
620 Compound Index

Pimaradiene-3{3,19-diol, ent-8(14),15- 1247 48, 126, 351
Pimar-8(9),15-diene, 20-hydroxy-7-oxo- 1249 48, 126,352
Pimar-8(9),15-diene, 18-hydroxy-ent- 1251 48, 127, 352
Pimara-8, 15-dien-19-oic acid, 7-oxo-ent- 821 48, 126,352
Pimara-9(1l)-en-19-oic acid, 12{3-acetoxy-ent- 823 48, 126, 352
Pimara-9(l1),15-dien-19-ol, ent- 1250 48, 126, 352
Pimar-9(11),15-dien malonate, 18-hydroxy-ent- 1252 48, 127,352
Pimar-9(11),15-dien malonate, 19-hydroxy-ent- 1253 48, 127, 352
Pimar-9(11),15-diene, 3a,19-dihydroxy-ent- 1254 48, 127, 352
Pimar-8(9), 15-diene, 20-hydroxy-7-oxo- 1249 48, 126, 352
Polyalthic acid 830 32, 99, 300
Polyalthic acid, 17-oxo-8{3,17-dihydro- 838 32, 99, 301
Polyalthic acid, 19-hydroxy- 835 32,99, 300
Polyalthic acid, 3a-[2-methylbutyryloxy]- 833 32,99,300
Polyalthic acid, 3a-angeloyloxy- 832 32, 99, 300
Polyalthic acid, 3a-hydroxy- 831 32, 99, 300
Polyalthic acid, 3a-isobutyryloxy- 834 32, 99, 300
Polyalthic acid, 8a, 17-epoxy-8, 17-dihydro- 836 32, 99, 300
Polyalthic acid, 8{3, 17-epoxy-8, 17-dihydro- 837 32, 99, 300
Polyalthine, 17-hydroxy-iso- 414 32, 99, 302
Polyalthine, 7{3-hydroxy-[Austrochaparol] 401 31,98,299
Printziaic acid lactone, 5a-hydroxy-5, 10-dihydro- 916 46, 121,344
Printziaic acid, 915 46, 121,343
5a-hydroxy-1 ,2-dehydro-5, 10-dihydro-
Printziaic acid, 5a-hydroxy-5, 10-dihydro- 913 46, 121,343
Printziaic acid, 5a-methoxy-5, lO-dihydro- 914 46, 121,343
Printzianic acid 571 45, 121,343
Printzianic acid, iso- 572 46, 121,343
Psiadiol 404 31,98, 300
Pulicaria angustifolia compound 1a 985 46, 122, 345
Pumiloxide, 6{3-hydroxy- 421 32, 99, 303
Rebaudioside A 685 53, 139, 371
Rebaudioside B 684 53, 139, 371
Rebaudioside D 688 53, 139, 371
Rebaudioside E 689 53, 139, 371
Relhania acid 231 21, 86, 263
Rimuen-18-yl acetate, 5{3-hydroxy-ent- 883 27, 93, 279
Rimuen-18-yl tiglate, 5{3-hydroxy-ent- 885 27, 93, 279
Rimuen-3a,5{3,18-triol, ent- 886 27,93,279
Rimuen-3a,5{3-diol, ent- 884 27, 93, 279
Rimuen-5{3,18-diol, ent- 882 27, 93, 279
Rimuen-5{3-ol, ent- 881 27, 93, 279
Rosa-1(l0), 15-dien-18-oic acid 890 27, 93, 280
Rosa-5,15-dien-18-yl-acetate, 3a-hydroxy- 889 27, 93, 279
Rosa-5, 15-dien-3a, 18-diol 887 27,93,279
Rosa-5, 15-dien-3a-yl acetate, 18-hydroxy- 888 27,93, 279
Compound Index 621

Royleanone 321 27,94,282
Royleanone, 7-acetoxy- 323 27, 94, 282
Royleanone, 7-keto- 324 27, 94, 283
Royleanone, dehydro- 322 27, 94, 282
Rugosolide 566 43, 117,334
Ruilopezia acid 1256 56, 136, 363
Salicifoliol 154 16, 74, 248
Salviarin 973 42, 119, 341
Salviarin, 6a-angeloyloxy-l-oxo-2,3-dihydro- 971 42, 119, 341
Salvic acid 1143 17,75,239
Salvic acid, 7a-acetyl- 1144 17,75,239
Salvicin 1223 44, 118, 323
Salvin 1234 45, 118, 330
Salvinin 1235 45, 118, 330
Sandaracopima-8( 14 )-en-6(J-D-glucoside, 922 26,91,277
15,16-dihydroxy-
Sandaracopimar-15-en-II-one, 297 26, 91, 274
12(J-acetoxy-8(J-hydroxy-
Sandaracopimar-15-en-ll-one, 8(J' 12a-dihydroxy- 296 25,91,274
Sandaracopimar-15-en-11-one, 8(J-hydroxy- 283 25,91,274
Sandaracopimar-15-en-3(J,18-diol 285 25,91,274
Sandaracopimar-15-en-6(J, 8(J' II a-triol 298 26, 91, 274
Sandaracopimar-15-en-6(J,8(J-diol 277 25, 90, 274
Sandaracopimar-15-en-8(J, II a-diol 279 25, 90, 274
Sandaracopimar-15-en-8(J,11a-diol, 293 25,91,274
12(J-(p-hydroxycinnamoyloxy)-
Sandaracopimar-15-en-8(J,11a-diol, 12(J-acetoxy- 292 25,91,274
Sandaracopimar-15-en-8(J, II a-diol, 588 48,91,274
12(J-acetoxy -[Structure incorrectly
drawn = Cmpd No. 292]
Sandaracopimar-15-en-8(J' 11 a-diol, 6{3-acetoxy- 299 26, 91, 274
Sandaracopimar-15-en-8{3,12a-diol, 11{3-acetoxy- 295 25,91,275
Sandaracopimar-15-en-8{3, 12{3-diol, 11 a-acetoxy- 289 25,91,274
Sandaracopimar-15-en-8{3-ol [Published structure 587 48,90,273
incorrectly drawn = Cmpd No. 276]
Sandaracopimar-15-en-8{3-ol, 11a, 12(J-diacetoxy- 294 25,91,274
Sandaracopimar-15-en-8{3-ol, 6{3-acetoxy- 278 25, 90, 274
Sandaracopimar-15-ene, 20-hydroxy-8{3,20-oxido- 287 25,91,275
Sandaracopimar-15-ene, 8{3, l1a, 12{3-trihydroxy- 288 25,91,274
Sandaracopimar-15-ene, 290 25,91,274
8{3,12{3-dihydroxy-1Ia-senecioyloxy-
Sandaracopimar -15-ene, 291 25,91,274
8{3,12{3-dihydroxy-lla-tiglinoyloxy-
Sandaracopimar-15-ene, 8(J ,20-dihydroxy- 286 25,91,275
Sandaracopimar-15-ene, 8(J-hydroxy- 276 25, 90, 273
Sandaracopimar-15-ene, 8(J-hydroxy-l1a-acetoxy- 282 25,91,274
Sandaracopimar-15 -ene, 280 25, 90, 274
8/3-hydroxy-llo:-senecioyloxy-
622 Compound Index

Sandaracopimar-15-ene, 281 25,91,274
8{3-hydroxy-lla-tiglinoyloxy-
Sandaracopimar-15-ene, 8{3-hydroxy-12{3-acetoxy- 284 25,91,274
Sandaracopimar-7, 15-dien-18-oic acid 301 26,91,273
Sandaracopimar-7, 15-dien-18-oic acid, 303 26,91,273
3{3-acetoxy-
Sandaracopimar-7 -ene, 306 25, 92, 276
3a, 15, 16-trihydroxy-13-epi-
Sandaracopimar-7-ene, 9a, 15, 16-trihydroxy- 307 26,92,276
Sandaracopimar-8( 14), 15-dien-18-oic acid 300 26,91,275
Sandaracopimar-8(14), 15-dien-18-oic acid, 302 26,91,275
3{3-acetoxy-
Sandaracopimar-8(14), 15-diene, 932 24,90,272
1{3,11a-diacetoxy-
Sandaracopimar-8( 14), 936 25, 90, 273
15-diene, 1{3,11a-diacetoxy-6,7-epoxy-
Sandaracopimar-8(14), 15-diene, 937 25, 90, 273
1{3,11a-diacetoxy-7-oxo-
1{3,11a-dihydroxy-
1{3,11a-dihydroxy-7a-acetoxy-
1{3, 7a, 11a-triacetoxy-
1{3,7a-dihydroxy-
1{3-hydroxy-7 a-acetoxy-
Sandaracopimar-8(14), 15-diene, 7a-hydroxy- 927 24,90,272
Sandaracopimar-8( 14), 15-diene, 934 25,90,272
7a-hydroxy-1{3,11a-diacetoxy-
7a-hydroxy-1{3-acetoxy-
Sandaracopimar-8( 14)-en-19-oic acid, 921 26,91,276
6{3, 15, 16-trihydroxy-
Sandaracopimar-8(14)-ene, 923 26,91,277
6a, 15, 16, 18-tetrahydroxy-
Sandaracopimaradiene 274 24,90,272
Sandaracopimaradiene, iso- 275 25, 90, 273
Schkuhriadiol, cyc1o- 463 36, 105,313
Schkuhriadiol-16-0-acetate, cyc1o- 464 36, 106,313
Schkuhrianol, acetate [16-acetoxy-14,15-epoxy- 457 37, 107,315
4,15-dihydro-13-epi-ent-Manoyl oxide]
Sc1areol 1102 16,74,247
Sc1areol, 6a-angeloyloxy- 153 16, 74, 247
Sc1areol, 8-epi-ent 450 34, 100, 308
Sempervirenic acid 113 14, 72, 242
[3{3-acetoxy-labda-7, 13-dien-15-oic acid]
Compound Index 623

Smallantha-2Z, lOE, 13E-triene, 981 9,64,227
1, 19-dihydroxy-6, 7-epoxy-12-oxo-
Smallantha-2Z, lOE, 14(21)-triene, 983 9,64,227
1, 19-dihydroxy-6, 7-epoxy-12-oxo-
Smallantha-2Z,6Z, lOE, 13E-tetraene, 980 9,64,227
1,19-dihydroxy-
Smallantha-2Z,6Z, lOE, 14(21)-tetraene, 982 9,64,227
1,19-dihydroxy-12-oxo-
Solidagenone 158 16, 74, 250
Solidagenone, 13-epi-dehydroxy- 194 18, 77, 253
9a, 13a-epoxy-13, 16-dihydro-
Solidagenone, 193 18,77,253
9-dehydroxy-9a, 13a-epoxy-13, 16-dihydro-
Solidago alcohol 241 23, 88, 265
Solidago alcohol, 8-epi- 238 22, 87,264
Solidago aldehyde 240 23, 88, 265
Solidago dialdehyde 243 23, 88, 265
Solidago epoxylactol 247 23, 88, 268
Solidago gigantea compound I 1062 23, 88, 265
Solidago gigantea compound II 1066 23, 88, 269
Solidago gigantea compound III 1063 23, 88, 265
Solidago gigantea compound IV 1064 23, 88, 241
Solidago gigantea compound V 1065 23, 88, 265
Solidago gigantea compound VI 1067 23, 88, 269
Solidago gigantea compound VII 1068 24,89,269
Solidago glycol 242 23, 88, 265
Solidago lactol 246 23, 88, 267
Solidago-18-oate, 251 39, 114, 322
methyl 8-epi-l,2-dehydro-
[Nidoreseda acid methyl ester]
Solidago-18-oic acid [Incorrectly drawn with 245 39, 114
C-8,8-methyl; probably the same as 249]
Solidago-IS-oic acid, 1,2-dehydro- 250 39, 114, 322
[Incorrectly drawn with C-8,8-methyl;
probably = 248]
Solidago-IS-oic acid, 8-epi 249 39, 113
Solidago-IS-oic acid, 8-epi-1,2-dehydro- 248 39, 113, 322
Solidagoic acid A 239 23, 88, 265
Solidagoic acid B 244 23, 88, 265
Solidagolactone [Soldagolactone I; 543 43, 116, 332
16-Hydroxy-kolavenic acid lactone]
Solidagolactone II [Elongatolide C] 258 22, 87,265
Solidagolactone II, 2a-hydroxy- 263 22, 87,265
Solidago virgaurea compound 4a]
Solidagolactone II, 3-oxo-3,4-dihydro- 268 23, 88,267
Solidagolactone II, 3,8,4a-dihydroxy-3,4-dihydro- 266 22,88,267
Solidagolactone III 259 22,87,265
Solidagolactone III, 2a-hydroxy- 264 22,87,265
624 Compound Index

[Solidago virgaurea compound 4c]
Solidagolactone III, 3-oxo-3,4-dihydro- 269 23,88,267
Solidagolactone III, 3a,4a-epoxy-3,4-dihydro- 261 22, 87, 266
Solidagolactone III, 3(J,4a-dihydroxy-3,4-dihydro- 267 22, 88, 267
Solidagolactone V 262 22,87,267
Solidagolactone V, 2(J-hydroxy- 265 22, 88,267
Solidagolactone VIII 988 23,88,266
Solidagolactone, tricyclo- 947 24,89,271
Solidagonal acid 960 47, 125,349
Solidagonic acid 962 42, 116,327
Solidagonic acid 500 40, 115,323
[7a-Acetoxy-13,14E-kolavenoic acid]
Stenolobin 639 51, 132, 358
Stenolobin, 15a-angeloyloxy- 1007 51, 133,361
[methyl-15a-angeloyloxy-
ent-kaur-16-en-19-oate]
Stephalic acid 570 44, 119, 338
Sterebin A 1157 21, 85, 262
Sterebin B 1158 21, 85, 262
Sterebin C 1159 21, 85, 262
Sterebin D 1160 21,85,262
Steviolbioside 682 53, 138, 371
Stevioside 683 53, 138, 371
Stevisalicinone 1026 28,95,284
Strictic acid 573 46, 122,345
Strictic acid, 12a-[2-methy1butyry1oxy]- 952 46, 122, 345
Symphyoreticulic acid, 13E- 537 42, 116, 325
Symphyoreticulic acid, 13Z- 536 42, 116,326
Terminaloic acid 759 56, 140,374
Tetrachyrin [Zoapatlin] 800 59, 146,382
Tomentanol 1099 11, 66, 231
Tomentol 1097 10, 66, 231
Tomentol, pre- 1094 9,64,228
Tomexanthin 56 10,66,230
Tomexanthol 1098 11, 66, 230
Tomexanthol, pre- 1096 7,61,222
Trachyloban-19-al, ent- 855 58, 144,380
Trachyloban-19-oic acid 791 58, 144,380
Trachyloban-19-oic acid, 7(J-hydroxy- 1259 58, 145,380
Trachyloban-19-oic acid, l1-oxo- 793 58, 144,380
Trachyloban-19-oic acid, 795 58, 145, 381
lla-[16' a-hydroxy-
ent-kaur-l1 ' -en-19' -oyloxy]-
Trachyloban-19-oic acid, 15a-acetoxy- 825 58, 144,380
Trachyloban-19-oic acid, 15a-ange1oy1oxy- 826 58, 144,380
Trachyloban-19-oic acid, 15a-isobutyry1oxy- 893 58, 144,380
Trachyloban-19-oic acid, 792 58, 144,380
7a-hydroxy-[Ciliarix acid]
Compound Index 625

Trachyloban-19-oic acid, 15a-isovaleryloxy- 827 58, 144,380
Trachylobanoic acid, 9, II-dehydro- 794 58, 145,380
Trachyloban-19-oic acid thujanol ester, ent- 856 58, 145, 381
Trachyloban-19-oic acid methyl ester 1204 58, 145,380
Tricyclosolidagolactone 947 24,89,271
Trinervinol 807 26,91,276
[lsopimara-8(14)-en-3/1, 15, 16, 17-tetrol]
Tucumanoic acid 962 40, 115,327
Turbinatone 1163 28, 94, 283
Viguieric acid 14 7,61,222
Villanovane, 877 59, 147, 383
13a,17-dihydroxy-19-(3-methylvaleryloxy)-
Villanovane, 875 59, 147,383
13a,17-dihydroxy-19-isovaleryloxy-
Villanovane, 17-acetoxy- 878 59, 147,383
13a-hydroxy-19-(3-methylvaleryloxy)-
Villanovane,
17-acetoxy-13a-hydroxy-19-isovaleryloxy- 876 59, 147,383
Villanovane, 17-acetoxy- 880 59, 147,383
13a-hydroxy-3a-(3-methylvaleryloxy)-
Villanovane, 17-acetoxy-13a-hydroxy- 879 59, 147,383
3a-isovaleryloxy-
Villanovane, 3a,15a-dihydroxy- 894 59, 147,383
Wedelia -seco-kaurenolide, 15 /1-hydroxy- 763 57, 141,374
Wedelia-seco-kaurenolide, 760 56, 141,374
9-oxo-[wedelia-seco-kaurenolide]
Wedelia-seco-kaurenolide, 9a-hydroxy-9-desoxo- 761 57, 141,375
Wedelia-seco-kaurenolide, 9/1-hydroxy-9-desoxo- 762 57, 141,375
Wedeloside 679 53, 137,370
Wedeloside, L-rhamnopyranosyl- 680 53, 137,370
Wederegiolide, 15a-hydroxy- 866 56, 141,374
Wederegiolide, 15/1-acetoxy- 868 56, 141, 374
Wederegiolide, 15/1-hydroxy- 867 56, 141,374
Wyethic acid 6 7, 60,219
Zoapatanol 55 10, 66, 230
Zoapatanol, pre- 1095 7, 61, 221
Zoapatlin,15-oxo- 847 59, 146, 382
Species Index
Alphabetized Listing of Species Names with Authorities
Abrotanella nivigena Muell., 178, 180 K. & R., 204

Acanthospermum australe (Loefl.) Aspilia floribunda (Gardn.) Baker,
Ktze., 152,213 181, 190,204
Acanthospermum hispidum DC., 154 Aspilia foliacea, 178, 181, 190
Achillea filipendula Lam., 165, 177 Aspilia jolvana, 178, 179, 181, 188
Achyrocline alata (H. B. K.) DC., 167 Aspilia mossambicensis, 181,205
Achyrocline vargasiana, 153 Aspilia ovalifolia, 177, 179, 181, 188
Acritopappus confertus (Gardn.) K. & Aspilia parvifolia Mattf., 171, 178,
R., 168, 171, 172, 175, 178,212 179, 181, 188, 190, 195, 196,
Acritopappus hagei K. & R., 169, 175, 213
176 Aspilia pluriseta Schweinf. subsp.
Acritopappus longifolius (Gardn.) K. & pluriseta, 179, 181, 185, 188,
R., 167, 168, 169, 175,204 189, 190, 195
Acritopappus morii K. & R., 168, 169, Aspilia riddellii, 181
215 Aster alpinus L., 208
Acritopappus teixeirae K. & R., 175, Aster bakeranus Burtt. Davy ex C. A.
176 Smith, 179, 181
Adenostemma caffrum DC., 191, 197 Aster pleiocepha1us, 181, 188
Adenostemma lavenia (L.) O. Kuntze, Aster tanacetifolius, 185, 187
191, 198 Athrixia arachnoidea Wood, 198
Ageratina dendroides (Spreng.) K. & Athrixia elata Sond., 172, 181, 191,
R., 167 198
Ageratina tristis (DC.) K. & R., 208 Athrixia phylicoides DC., 198, 199
Ageratum fastigiatum (Gardn.) K. & Athrixia pinifolia N. E. Br., 178
R., 168, 169, 199 Atractylis gummifera L., 191, 199
Ambrosia hispida Pursh, 193 Austrobrickellia patens (D. Don. ex H.
Amphiachyris dracumculoides, 191 & A.) K. & R., 209
Arctotheca prostata, 180 Austroeupatorium chaparense (B. L.
Arctotis revo1uta Jacq., 178, 179, 180, Robins.) K. & R., 166, 169
186, 196 Austroeupatorium inulaefolium (H. B.
Aristeguietia buddleaefolia (Benth.) K. K.) K. & R., 169, 170, 178,
& R., 157, 160 179, 181, 185, 187, 189, 194,
Aristeguietia pseudoarborea (Hieron.) 196, 202, 216
Species Index 627
Ayapana amygdalina (Lam.) K. & R., 173,217

167, 172,216 Baccharis rhomboidalis, 217
Baccharis alaternoides, 172, 176 Baccharis salicifolia Blake, 155, 174,
Baccharis articulata Lam (Persoon), 205,210,211,212,215,216,
173, 174,217 217
Baccharis calvescens DC., 174 Baccharis salzmannii DC., 181, 188
Baccharis cassinaefolia DC., 174, 175 Baccharis sarothroides A. Gray, 174,
Baccharis chilco H. B. K., 174 210
Baccharis concinna Barrosa, 185, 187, Baccharis scoparia (L.) Sw., 154, 207,
190 211
Baccharis concinnia Barrosa, 181 Baccharis sternbergiana Steud., 166,
Baccharis conferta H. B. K., 174 167
Baccharis crispa, 174 Baccharis subdentata DC., 174
Baccharis eggersii Hieron, 207 Baccharis tola, 160, 171, 199,200
Baccharis elliptica, 181, 188, 195 Baccharis tricuneata (L.f.) Pers. var.
Baccharis genistelloides (Lam.) Per., tricuneata, 173, 174
175 Baccharis tricuneata var. lineata
Baccharis gilliesii, 174 Cuatr., 173, 174
Baccharis grandicapitulata Hieron, 207, Baccharis trimera (Less.) DC., 175,
217 176
Baccharis hutchisonii Cuatr., 173, 207 Baccharis trinervis Pers., 153,215
Baccharis incanum, 173, 203 Baccharis truncata Gardn., 176, 179,
Baccharis incarum Wedd., 216, 217, 181, 186, 188
218 Baccharis tucumanensis H. & A., 155,
Baccharis intermixta Gardn., 167, 181, 207
185 Baccharis vaccinioides H. B. K., 210
Baccharis kingii Cuatr., 203 Bahianthus viscidus (Baker) K. & R.,
Baccharis macraei, 173, 174 176
Baccharis magellanica (Lam.) Pers., Balsamorhiza sagittata (Push.) Nutt.,
174,217 178,207
Baccharis microcephala (Less.) DC., Bedfordia salicinia DC., 162, 184
175 Bejaranoa ba1ansae (Hieron.) King et
Baccharis min uti flora Mart., 178, 179, Robins., 213
181, 194, 195, 196, 197 Bejaranoa semistriata (Baker) K. & R.,
Baccharis nitida (R. & R.) Pers., 207 150
Baccharis oxydonta DC., 171 Bishovia boliviensis K. & R., 157
Baccharis pingraea DC., 214, 215, 216 Brickellia annulosa (DC.) A. Gray, 173
Baccharis pithieri, 188 Brickellia argyrolepis B. L. Robins.,
Baccharis polifera Griseb., 216 154, 155
Baccharis polyphylla Gardn., 176, 181, Brickellia corymbosa (DC.) A. Gray,
185, 187, 190 155
Baccharis pylicoides, 181 Brickellia diffusa A. Gray, 154, 161
Baccharis quitensis H. B. K., 178, Brickellia eupatoriedes (L.) Shinner,
179, 181, 194, 197 154, 155, 177
Baccharis ramosissima Gardn., 179, Brickellia paniculata (Mill.) B. L.
181, 190 Robins., 155
Baccharis rhetinodes Meyen. et Walp., Brickellia squarrosa (Cav.) B. L.
174 Robins., 155
Baccharis rhetinoides Meyen. et Walp., Brickellia vernicosa B. L. Robins.,
628 Species Index
155, 208 Conyza stricta Willd., 162, 169, 176

Brickellia veronicaefolia (H. B. K.) A. Conyza ulmifolia, 153
Gray, 155, 156 Critonia daleioides DC., 178, 181,202
Brickellia veronicaefo1ia A. Gray var. Critonia canescens
typica, 156, 161 Critonia hebebotrya, 181, 202
Caca1ia bu1bifera, 178, 180, 181, 196 Cronquistianthus bishopii K. et R.,
Campovassouria bup1eurifolia (DC.) K. 212, 213
& R., 178, 179, 180, 181, 189, Croptilon divaricatum, 165
190, 191 Denekia capensis Thunb., 156, 171,
Caramboa pithieri, 178, 181, 187 208, 212
Caramboa trugillensis, 181 Desmanthodium fruticosum, 169
Carterothamnus anomalochaeta R. M. Dimerostemma asperatum Blake, 153
King, 154, 185 Dimerostemma brasilianum Cass., 153
Centaurea cineraria, 153 Dimorphotheca aurantiaca Hort., 199,
Centipeda orbicularis Lour., 153, 162 200
Chiliotrichium rosmarinifo1ium Less., Dimorphotheca pluvialis Moench., 165,
213,216,217 166
Chromolaena collina (DC.) K. & R., Dimorphotheca pseudoaurantiaca Sch.
156 & Thell., 199,200
Chromolaena cryptantha, 181 Disynaphia halimifolia (DC.) K. & R.,
Chromolaena laevigata (Lam.) K. & 150
R.,210 Disynaphia multicrenulata, 178, 180,
Chrysanthemoides inc ana T. Norl., 165 181, 185, 187, 189, 195,208
Chrysanthemoides mono1ifera (L.) T. Doronicum hungaricum, 192
Norl., 164, 165 Doronicum macrophyllum Fisch., 207
Chrysanthemoides monolifera (L.) T. Doronicum microphyllum
Nor!. subsp. canescens (DC.) T. Echinacea purpurea Moench., 160
Nor!., 163, 164, 165 Enhydra fluctuans Lour., 181, 185,
Chrysothamnus nauseusus (Pall.) Britt., 187, 189, 196
155, 156, 159, 214 Erigeron philade1phicus L., 171
Chrysothamnus paniculatus (Gray) Espeletia curial ens is , 186
Hall, 157, 158, 159, 160, 161, Espe1etia figueirasii, 181, 194
163 Espe1etia floccosa, 181, 194
Chrysothamnus viscidiflorus, 166 Espeletia garciae Humb. & Bonp!.,
Coespe1etia lutescens (Cuatr. & Arist.) 178, 180, 181
Cuatr., 171, 178, 180, 181, 185, Espeletia grandiflora, 178, 180, 181,
186, 191, 193, 194, 198 185
Coespeletia marc ana Cuatr., 178, 180, Espeletia hartwegiana, 171, 180, 186,
181, 185, 186, 191, 193, 194, 192, 198
196, 198 Espeletia humbertii, 186, 196
Coespeletia moritziana (Sch. Bip.) Espeletia littlei, 186, 192, 196
Cuatr., 171, 178, 180, 181, 186, Espeletia moritziana, 181, 194
188, 189, 192, 194, 198 Espeletia neriifolia, 180, 192
Conyza canadensis, 153 Espeletia schultzii Wedd., 178, 180,
Conyza ivaefolia, 174 181, 186, 192, 196
Conyza japonica (Thundb.) Less., 173, Espeletia tenor, 186
176 Espeletia timotensis, 192
Conyza podocephala DC., 153, 174 Espeletia uribei Cuatr., 178, 180, 181,
Conyza scabrida DC., 174, 176,203, 186, 192, 193, 194, 195
205, 206 Espeletia weddellii Sch. Bip. ex Wed.,
Species Index 629
186, 192 Geigeria burkei Harv. subsp. burkei

Espeletia wedellii Sch. Bip., 178, 180, var. elata Merxm., 151
207 Geigeria burkei Harv. subsp. burkei
Espeletiopsis garciae Cuatr., 178, 181, var. intermedia (S. Moore)
186, 188, 189, 192 Merxm., 151, 156
Espeletiopsis glandulosa Cuatr., 178, Geigeria burkei Harv. subsp. burkei
181, 186, 188, 189, 192, 193, var. zeyheri (Harv.) Merxm.,
198 151, 152, 156
Espeletiopsis guacharaca (Diaz) Cuatr., Geigeria burkei Harv. subsp. diffusa
171, 178, 179, 180, 181, 186, (Harv.) Merxm., 151
189, 191, 192, 193, 194, 196, Geigeria burkei Harv. subsp.
198 fruticulosa Merxm., 150, 151
Espeletiopsis purpurascens Cuatr., 178, Geigeria glabra var. glabra
181, 186, 188, 189, 192, 193, Gnaphalium guadichaudianum, 171
194, 196, 198 Gnaphalium microcephalum, 153
Espeletiopsis tachirensis (Aristeg.) Gnaphalium oligandrum (DC.) Hilliard
Cuatr., 178, 181, 186, 188, 190, & Burtt, 181, 192
192, 193, 194, 196, 198 Gnaphalium undulatum L., 171, 176,
Eupatorium album L., 191,201 178, 180, 181, 186, 199
Eupatorium deltoideum, 192 Gochnatia glutinosa Don., 217
Eupatorium inulaefolium H. B. K., Gochnatia paniculata (Less.) Cabrera,
201, 209 172, 173, 174
Eupatorium jhanii B. L. Robins., 160, Goyazianthus tetrastichus (B. L.
206 Robins.) K. & R., 172, 178,
Eupatorium maretiana 180, 181, 187, 190, 192, 195,
Eupatorium petaloideum Britt., 167, 217
202, 218 Grangea maderaspatana Poir, 162, 178
Eupatorium petiolare Moc. & Ses. ex Grazielia dimorpholepsis (Baker) K. &
DC., 181 R., 170, 181, 188
Eupatorium salvia, 214 Grazielia intermedia (DC.) K. & R.,
Eupatorium turbinatum Gray, 175, 150, 180, 181, 188, 189, 190
214, 216 Grazielia serrata (Spreng.) K. & R.,
Eupatorium villosum Sweet, 206 181, 188, 191
Felicia erigeroides, 153 Greenmaniella resinosa, 153
Fleischmannia deborabellae K. & R., Grindelia acutifolia, 158, 159, 161
156 Grindelia aegialitis Gabr., 166, 214
Fleischmannia pycnocephaloides (B. L. Grindelia aphanactis Rydb., 158, 159
Robins.) K. & R., 156 Grindelia boliviana Rusby, 157, 158,
Fleischmannia sinclairii (Benth. in 210,211,215
Oerst) K. et R., 173 Grindelia camporum Greene, 157, 158,
Fleischmannia viscidipes (B. L. 159, 160
Robins.) K. & R., 203, 204 Grindelia chi1coensis (Corub.) Cabrera
Garuleum bipinnatum Less., 163, 164, Grindelia chiloensis, 157, 158, 159,
165 160
Garuleum pinnatifidum DC., 163, 164, Grindelia discoidea Hook. & Am.,
165 155, 214
Garuleum sonchifolium (DC.) T. Grindelia humilis (Hook. & Am.), 158
Norl., 163, 165, 176,200 Grindelia nauseosus, 158
Geigeria burkei Harv. subsp. burkei Grindelia paludosa Greene, 157, 158,
var. burkei, 150, 151, 152 159, 161
630 Species Index
Grindelia perennis A. Nels., 158, 159 187, 189, 194, 196, 199,200,
Grindelia pulchella, 157, 158, 159, 160 201, 202, 203
Grindelia robusta, 158, 159, 160 Helianthus argophyllus T. & G., 196,
Grindelia squarrosa (Pursh.) Dunal, 201
157, 158, 159, 160, 207 Helianthus californicus DC., 201
Grindelia stricta DC., 157, 158, 159, Helianthus ciliaris DC., 201
160, 161 Helianthus debilis Nutt. subsp.
Gutierrezia dracunculoides (DC.) cucumerifolius (T. & G.) Heiser,
Blake, 157, 163 182, 186, 187, 189, 194, 195,
Gutierrezia gilliesii Griseb., 208, 210 196, 197,200
Gutierrezia grandis S. F. Blake, 203, Helianthus debilis Nutt. subsp. debilis,
208 182, 187,201
Gutierrezia lucida Greene, 156, 157 Helianthus decapetalus L., 170, 182,
Gutierrezia mandonii (Sch. Bip.) 185, 200, 212
Solbrig, 157 Helianthus decapetalus var. multiflorus
Gutierrezia sarothrae (Pursh.) Britt. & A. Gray, 212
Rusby, 202, 203 Helianthus giganteus L., 179, 182,
Gutierrezia solbrigii, 208, 210, 213, 192, 200
215 Helianthus grosseseratus, 194,201,
Gutierrezia spaerocephala Gray, 154, 218
214 Helianthus grosseserratus Martens,
Gutierrezia spathulata (Phil.) Kurtz, 186, 192
210, 216 Helianthus heterophyllus Nutt., 182,
Gutierrezia texana (DC) T. & G., 211, 192, 193, 194
212 Helianthus hirsutus Raf., 182, 200,
Gymnosperma glutinosa, 154 202, 212
Haplopappus angustifolius, 176 Helianthus laciniatus, 218
Haplopappus ciliatus (Nutt.) DC., 173 Helianthus maximiliani Schrader, 170,
Haplopappus foliosus, 176 192, 193
Haplopappus glutinosus Cass., 210 Helianthus niveus subsp. canescens (A.
Haplopappus paucidentatus Phil., 211, Gray) Heiser, 182, 186, 201
216 Helianthus nuttallii T. & G., 182
Haplopappus pectinatus Phil., 167, Helianthus nuttallii T. & G. subsp.
210, 215 nuttallii, 186, 194, 201
Haplopappus tenuisectus, 158 Helianthus occidental is Riddell, 170,
Haplopappus venetus Blake, 158 182, 186, 187, 190, 194, 195,
Hartwrightia floridana Gray, 167, 172, 196, 197,200,201
173 Helianthus occidentalis var.
Hebeclinium macrophy llum (L.) DC., dowellianus, 182, 188, 194, 195,
209 200
Helianthopsis bishopii H. Robins., 181, Helianthus petiolaris Nutt., 182, 186,
199, 200, 207 194, 197,201,202
Helianthopsis microphylla (H. B. K.) Helianthus radula (Pursh) T. & G.,
H. Robins., 181, 199,200 182, 185, 187, 194, 195, 196,
He1ianthopsis utcubambensis H. 197, 198,201
Robins., 181, 199,200 Helianthus rigidus (Cas.) Desf., 182,
Helianthus angustifolius L., 170, 182, 196,201,212,218
187, 196 Helianthus salicifolius A. Dietr., 196,
Helianthus annuus L., 180, 182, 186, 201
Species Index 631
Helianthus simulans E. E. Wats., 182, 185, 186, 196

185, 186, 187, 195, 197 Helichrysum pilosellum (L.f.) Less.,
Helianthus strumosus L., 177, 202 179, 180, 182, 185, 192
Helianthus tomentosus Elliot, 201 Helichrysum pinifolium (Lam.)
Helianthus tuberosus L., 170, 182, Schrank, 157, 171
185, 188 Helichrysum platypterum DC., 182,
Helichrysum acutatum DC., 153,212 192
Helichrysum albirosulatum Kill., 171, Helichrysum refluxum N. E. Br., 182,
212 192, 196, 199,201,208
Helichrysum argentissimum Wood, 182 Helichrysum ruderale Hilliard &
Helichrysum argyrolepis, 182, 216 Burth., 185, 192
Helichrysum aureum (Houtt.) Merile Helichrysum setosum Harv., 217, 218
var. monocephalum (DC.) Helichrysum subfacultatum Hilliard,
Hilliard, 182, 184, 185, 186, 192 153
Helichrysum bellum Hilliard, 182 Helichrysum subfalcatum Hilliard, 151
Helichrysum calliconum Harv., 153 Helichrysum subulifolium Hary, 182
Helichrysum chionosphaerum DC., Helichrysum suterlandii Harv., 156,
177, 182, 200, 201 170
Helichrysum confertum N. E. Br., Helichrysum vernum Hilliard, 157,
156, 167, 170, 182,208,212, 171, 179, 182
214 Hemizonia congesta DC., 154
Helichrysum cooperi Harv., 182, 184, Hemizonia lutescens (Greene) Keck,
185 153, 154
Helichrysum coriaceum, 157 Heterochrysum oreophilum, 213
Helichrysum davyi, 178, 179, 180, Heterocondylus grandis, 182
182, 185, 196 Heteromma simplicifolium, 153
Helichrysum dendroideum N. H. Heteropappus altaicus (Willd.)
Wakefield, 179, 184, 194, 199 Novopokrov, 173, 174,207
Helichrysum diosmifolium (Vent.) Heterotheca subaxillaris, 158, 160
Sweet, 165, 197 Hinterhubera imbricata Cuatr., 173,
Helichrysum fulvum N. E. Br., 182, 174
199, 201 Hofmeisteria fasciculata (Benth.)
Helichrysum heterolasium Hilliard, Walp., 156
179, 180, 182, 184, 185, 186 Hymenopappus newberryi (Gray) T.
Helichrysum Krebsianum Less., 151, M. Johnst., 197
153 Ichthyothere connata Blake, 169, 170,
Helichrysum miconiifolium DC., 179, 182, 188, 189
180, 182, 186 Ichthyothere cunabi, 182
Helichrysum mimetes S. Moore, 150 Ichthyothere latifolia (Benth.) Gardn.,
Helichrysum mundii Harv., 150 170, 182, 188, 189
Helichrysum nanum, 151 Ichthyothere rufa Gardn., 179, 182,
Helichrysum nudifolium (L.) Less., 188, 189
153 Ichthyothere terminalis (Spreng.)
Helichrysum nudifolium (L.) Less. var. Malme, 170, 179, 180, 182, 186,
nudifolium, 157, 214 187, 188, 189, 190, 191, 192,
Helichrysum odoratissimum Sweet, 153 193, 194, 196, 197, 199
Helichrysum oreophilum Klatt., 151 Ichthyothere ulei Thunb., 152, 180,
Helichrysum oxyphyllum Klatt., 151 182, 187, 188, 190
Helichrysum pallidum DC., 180, 182, Inula crithmoides, 156
632 Species Index
Inula royleana DC., 166, 201 Melampodium perfoliatum (Carv.) A.

Isocoma coronopifolia Greene, 158, Gray, 182, 206
159, 214 Mikania alvimii K. & R., 170, 172,
Isostephane heterophylla, 182 177,215
Kingianthus paradoxus H. Robins., 150 Mikania arrojadoi Mattf., 179, 180,
Koanophyllon admantium (Gardn.) K. 182, 184, 185, 186, 187, 189,
& R., 150, 162, 173 194, 195,201
Koanophyllon conglobatum (DC.) K. & Mikania banisteriae DC., 170, 178,
R., 150, 156, 157, 161, 162 184, 185, 202, 206
Lagascea rigida (Cav.) Stuessy, 182, Mikania belemii K. & R., 179, 180,
188, 192 182, 189
Lasianthaea podocephala (A. Gray) K. Mikania congesta DC., 209
Becker, 182, 192,206 Mikania cordata (Burm. f.) B. L.
Lasiolaena morii K. & R., 150 Robins., 183, 189
Lasiolaena santosii K. & R., 150, 167 Mikania goyazensis (B. L. Robins.) K.
Liatris elegans (Walt.) Michx., 153 &R., 150
Liatris laevigata Nutt., 177 Mikania hirsutissima DC. var.
Liatris scariosa Willd., 173 hirsutissima, 183
Liatris spicata (L.) Willd., 174,211 Mikania luetzelburgii Mattf., 179, 180,
Libanothamnus granatesianus Cuatr., 183, 186, 189, 194, 195
178, 179, 182, 186, 189, 198 Mikania micrantha, 180, 183
Libanothamnus neriifolia (B. ex H.) Mikania monagasensis, 183
Ernst, 179, 180, 182, 187, 192 Mikania mongenansis
Libanothamnus occultus (Blake) Cuatr., Mikania oblongifolia DC., 189
171, 182, 187, 192 Mikania officinalis Mart, 150, 151
Libanothamnus spectabilis (Cuatr.) Mikania periplocifolia Hook. et Am.,
Cuatr., 171, 182, 187, 192 213
Libanothamnus tamanus (Cuatr.) Mikania pyramidata Donn. Smith, 165,
Cuatr., 178, 182, 187, 192, 198 170, 171, 177
Libanothamnus wurdackii (R. T. & L. Mikania schenkii, 183
F.) Cuatr., 171, 178, 182, 187, Mikania sessilifolia DC., 150, 152,
192, 198 179, 180, 183, 184, 189, 191,
Lindheimera connata, 160 195
Lindheimera texana Gray et Engelm., Mikania triangularis Baker, 202, 217
160, 214 Montanoa atriplicifolia (Pers.) Sch.
Loxothysanus sinuatus (Less.) B. L. Bip. in Seeman, 183
Robinson, 182, 189 Montanoa frutescens, 183, 189
Lychnophora sellowii Sch. Bip., 178 Montanoa leucantha (Lag.) Blake
Macowania glandulosa N. E. Br., 155, subsp. arborescens (DC.) Funk,
162, 207 152
Madia sativa Mol., 154 Montanoa leucantha (Lag.) Blake
Melampodium diffusum Cass., 152 subsp. leucantha, 152
Melampodium divaricatum (Rich. in Montanoa mollissima Brongn. ex
Pers.) DC., 172,206 Groenl., 152
Melampodium leucanthum Torr. & Montanoa pteropoda Blake, 178, 179,
Gray, 209 180, 183, 187, 189, 192, 193
Melampodium longipilum Robins., 152 Montanoa tomentosa Cerv. in Llave &
Melampodium paludosum, 206 Lex. subsp. tomentosa, 152, 178,
Melampodium paniculatum, 182 180, 212
Species Index 633
Montanoa tomentosa Cerv. subsp. Osteospermum scariosum (DC.) Nor!'

microcephala (Sch. Bip.) Funk, subsp. scariosum, 164
152 Osteospermum subulatum DC., 165
Montanoa tomentosa Cerv. subsp. Osteospermum thodei Maikotter, 164,
xanthiifolia (Schultz Bip. in C. 165
Koch) Funk, 152, 183, 187, 189, Othonna cylindrica DC., 177, 183, 192
192, 199,201,206,207 Othonna floribunda Schltr., 177, 183
Morithamnus crassus K. & R., 166, Othonna sedifolia, 163, 171, 183, 194,
167, 172, 175, 196 195
Nardophyllum lanatum (Meyen.) Oxylobus adscendens, 207
Cabrera, 216 Oxylobus arbutifolius (H. B. K.) A.
Neomiranda angularis, 173 Gray, 154, 207
Nidorella agria Hilliard, 162 Oxylobus canescens, 203
Nidorella anomala Steetz, 199, 200 Oxylobus glanduliferus (Sch. Bip.)
Nidorella auriculata DC. subsp. Gray, 154, 214
polycephala (DC.) Willd., 153, Oyedaea boliviana Britton, 183, 190,
156 192
Nidorella hottentotica, 161 Oyedaea buphthalmoides, 180, 183,
Nidorella resedifolia DC., 162 187, 192, 196
Nordophyllum lanatum, 213 Oyedaea lanceolata (Russby) Blake,
Olearia heterocarpa S. T. Blake, 175 179, 180, 183, 190, 192
Olearia muelleri (sond.) Benth., 174 Oyedaea rusbyi, 179, 180, 183, 187,
Olearia paniculata, 171 190, 191, 192
Ophryosporus chi1ca (H. B. K.) Oyedaea verbesinoides, 179, 183, 186,
Hieron., 203 188
Osteospermum auriculatum (S. Moore) Palafoxia arid a B. L. Turner & M. I.
Nor!., 163, 164, 165 Morris, 177
Osteospermum barberiae (Harv.) Nor!., Palafoxia rosea (Bush.) Cory, 156,
153, 163, 164 160, 163, 165, 166, 215, 216
Osteospermum ciliatum Berg., 163, Palafoxia texana DC., 214
164, 165 Palafoxia texana var. ambigua, 156
Osteospermum corymbosum L., 163, Pegolettia senegalensis Cass, 150
164, 165 Perymeniopsis ovalifolia, 183, 189
Osteospermum fruticosum (L.) Nor!., Perymenium discolor, 183, 196
163, 164 Perymenium ecuadoricum Blake, 179,
Osteospermum incanum, 164 180, 183, 187, 195, 196
Osteospermum jucundum, 163, 164, Perymenium featherstoni, 179, 183,
165 187
Osteospermum junceum Berg, 163, Perymenium klattianum Fay, 180, 183,
164, 165 192, 193, 200, 206
Osteospermum muricatum E. Mey ex Perymenium ovalifolia (A. Gray) H.
DC. subsp. muricatum, 163, Robins., 187
164, 166 Perymenium serratum, 179, 183, 196
Osteospermum oppositifolium (A it. ) Peteravenia malvaefolia, 197, 200
Nor!., 164 Peteravenia schultzii, 200
Osteospermum polygalioides L., 164, Piptothrix jaliscensis B. L. Robins.,
165 209
Osteospermum rotundifolium (DC.) T. Piptothrix sinaloae Blake, 209
Nor!., 163, 164, 165 Piqueria trinervia Cav., 202
634 Species Index
Plagiocheilus prostratus Benth., 153 172

Planaltoa lychnophoroides Barroso, 169 Sciadocephala schultze-rhonhofiae
Pleurocoronis pluriseta (Gray) Matt., 185
K. & R., 154, 167 Senecio asperulus, 200
Podachaenium eminens, 156 Senecio erosus Wedd., 155
Polymnia canadensis L., 195 Senecio hypochoerideus DC., 217
Polymnia fruticosa H. B. K., 179 Senecio pseudoorientalis, 153
Polymnia fruticosum Benth., 179, 183, Senecio sandersonii Harv., 165
187 Senecio subrubriflorus O. Hoffm., 163,
Polymnia maculata Cav. var. maculata, 164, 165
183, 192 Senecio trichopterygius, 153
Polymnia pyramidalis Triana, 179, Senecio variabilis, 163
183, 187 Sigesbeckia orientalis L., 177
Printzia laxa N. E. Br., 171, 173, 174, Sigesbeckia pubescens Makino, 177,
175, 176 197,206,207
Psiadia altissima, 169 Silphium asteriscus L., 160, 161
Pulicaria angustifolia DC., 206, 208 Silphium compositum, 160
Pulicaria gnaphaloides (Vent.) Boiss., Silphium connatum, 156
174 Silphium integrifolium Michx., 160,
Pulicaria salviifolia Bgl. in Mem., 216, 161
217 Silphium perfoliatum L., 160, 161
Re1hania acerosa (DC.) Bremer, 161, Silphium terebinthinaceum Jacq., 160,
166, 167 161
Riencourtia oblongifolia, 192 Simsia dombeyana, 183
Robinsonia gayana, 196 Simsia holwayi, 183
Robinsonia thurifera, 183 Smallanthus fruticosus (Benth.) H.
Rudbeckia fulgida Ait. var. fulgida, Robins., 157, 179, 180, 183,
208 185, 187, 192, 194, 195
Ruilopezia bromeloides, 179, 183, 188, Smallanthus glabratus (DC.) H.
192 Robins., 180, 183, 185,206,208
Ruilopezia figueirasii, 179, 180, 185, Smallanthus reparius (H. B. K.) H.
187, 192, 198 Robins., 183, 185, 187
Ruilopeziajahnii (St.) Cuatr., 178, Smallanthus siegesbeckia, 183, 185,
179, 183, 184, 186, 187, 189, 187
192, 194, 196, 198 Smallanthus uvedalia (L.) Mackenzie,
Ruilopezia lindenii (Sch. Bip.) Cuatr., 179, 180, 183, 184, 185, 187,
178, 179, 180, 183, 186, 187, 195
188, 190, 192, 193, 194, 196, Solidago altissima L., 162, 163, 173,
198 175,207,208
Ruilopezia marcescens, 178, 180, 187, Solidago arguta Ait., 173, 176
190, 192, 193, 194, 198 Solidago canadensis L., 157, 160, 167,
Ruilopezia margarita Cuatr., 192, 196, 174
218 Solidago drummondii Torr. et Gray,
Ruilopezia marcescens 213
Ruilopezia paltonioides, 178, 179, 180, Solidago elongata Nutt., 172, 173, 175
183, 188, 192, 194, 195, 198 Solidago flexicaulis L., 213
Ruilopezia ruizii, 178, 183, 186, 188, Solidago gigantea, 157
190, 192, 193, 194, 195, 198 Solidago gigantea Ait. var. serotina,
Schkuhria multiflora H. & A., 171, 162,211
Species Index 635
Solidago itatiayensis (Hieron.) K. & B. L. Robins., 172, 175

R.,176 Symphyopappus reticulatus Baker, 172,
Solidago juncea Ait., 173, 174, 183, 173, 175,209
211 Tamania chardonii, 178, 179, 187,
Solidago missouriensis Nutt., 166, 171, 188, 189, 198
177, 183,209 Tetrachyron manicata, 183, 187, 192,
Solidago multiradiata, 183 193
Solidago multiradiata var. multiradiata, Tetrachyron orizabaensis Sch. Bip. ex
180 Klatt. var. websteri Wussow &
Solidago nemoralis Ait., 178 Urbatsch, 183, 187, 201
Solidago petradoria Blake, 158, 210 Tithonia longiradiata, 183, 193
Solidago racemosa Greene, 213 Trichogonia salvaiaefolia Gardn., 204
Solidago rigida L., 183 Trichogonia villosa (DC.) Sch. Bip.,
Solidago rugosa Mill., 163, 174, 175, 204,205
176, 178, 180, 183, 190 Trichogoniopsis morii K. & R., 150,
Solidago sempervirens, 155, 157 155, 160, 197
Solidago serotina Ait., 162, 211 Tridax peruviensis Powell, 208
Solidago Shortii Torr. & Gray, 175 Verbesina angustifolia (Benth.) Blake,
Solidago virgaurea L., 162, 163, 208 183, 193
Steiractinia mollis Blake, 179, 180, Verbesina oncophora Rob. & Seat,
183, 187, 190, 192, 196, 197 184, 193, 196
Steiractinia sodiroi (Hieron.) Blake, Vernonia divaricata, 184
179, 183, 192, 196 Vernonia glabra (Steetz) Vatke var.
Stevia andina, 156, 170, 183,209 glabra,213
Stevia aristata, 170, 200, 202 Vernonia venosissima, 184
Stevia berlandiera A. Gray, 156, 163, Viguiera bishopii H. Robins., 169,
170, 209 171, 184, 193, 196,200,201
Stevia bupthalmiflora, 188, 189 Viguiera cordata, 184
Stevia eupatoria Will, 185, 209 Viguiera cordifolia Gray, 184,200
Stevia jaliscensis B. L. Robins., 155 Viguiera dentata (Cav.) Spreng., 184,
Stevia lemmonia A. Gray, 209 186, 187, 193,201,208,209
Stevia lucida Lag. var. Bipontini, 169 Viguiera excelsa (Willd.) B. & H.,
Stevia monardaefolia H. B. K., 156, 184, 193, 194, 197,209
157, 183, 187 Viguiera excelsea (Willd.) B. & H.,
Stevia myriadenia Sch. Bip. ex Baker, 193
150, 151, 169, 173, 183, 188, Viguiera grammatoglossa DC., 179,
200 180, 184, 193, 199, 200
Stevia origanoides H. B. K., 170,202 Viguiera hypargyrea, 184, 190, 194
Stevia ovata Lag., 205 Viguiera incana, 184
Stevia paniculata Lag., 205 Viguiera insignis Miranda, 184, 193,
Stevia polycephala Bertol, 176 199, 200, 202
Stevia rebaudiana Bertoni, 160, 170, Viguiera lanceolata Britt., 201
191,214 Viguiera latibracteata, 193, 194, 195,
Stevia salicifolia Cav., 155, 157, 163, 197,201
170,209 Viguiera linearifolia, 184
Stevia setifera Rusby, 183 Viguiera linearis, 184, 193, 196
Stylotrichium rotundifolium Mattf., Viguiera maculata Blake, 184, 186,
150 203
Symphyopappus compressus (Gardn.) Viguiera oaxacana (Greenm.) Blake,
636 Species Index
184, 193 187, 188, 189, 190, 193, 199,

Viguiera pazensis Rusby, 184, 187, 200
188, 189, 199,200,201,202, Wedelia pinetorum, 188, 190
205 Wedelia regis H. Rob., 204
Viguiera porteri (A. Gray) Blake, 184, Wedelia scaberrima Benth., 184, 186,
186, 189, 190, 194 188
Viguiera potosina Blake, 184, 186, 208 Wedelia speciosa, 184
Viguiera procumbens (Pers.) Blake, Wedelia trilobata (L.) Hitch., 184,
184, 193, 201 185, 189, 190, 193, 199
Viguiera quinqueradiata (Cav.) A. Wedelia villosa, 184, 188
Gray, 187, 188 Wulffia maculata, 184
Viguiera stenoloba, 170, 185, 196,209 Wyethia helenioides (DC.) Nutt., 150
Viguiera stenoloba var. chihuahuense, Xanthium strumarium L., 191
193 Xanthium strumarium L. var.
Viguiera trichophylla, 184, 190, 201 strumarium, 191
Villanova titicaensis Meyer & Walp., Xanthocephalum linearifolium
204 Greenm., 168, 169
Wedelia asperrima Benth., 191 Zaluzania angusta, 180, 184
Wedelia buphthalmiflora Lorentz, 184, Zaluzania angustifolia, 196
187, 188, 189, 193 Zaluzania cinarescens, 184, 196
Wedelia calycina L. C. Rich in Pers., Zaluzania discoidea, 184, 193
184, 186, 187, 189, 190, 193, Zaluzania subcordata, 180, 184, 193
197,202 Zaluzania triloba, 184, 193
Wedelia glauca (Ort.) Hoffmann ex Zexmenia gnaphaloides Gray, 150,
Hicken, 184, 189, 191 153, 166
Wedelia grandiflora Benth., 179, 180, Zexmenia hispida A. Gray, 184, 193
184, 185, 187, 188, 189, 190, Zexmenia phyllocephala (Hemsl.)
193, 196 Staad. & Steyer, 206
Wedelia helianthoides H. B. K., 184, Zexmenia pinetorum, 188
188, 190, 193, 194, 195 Zinnia tenuiflora J acq ., 150
Wedelia hispida H. B. K., 184, 193 Zinnia verticillata Andr., 150
Wedelia hookeriana Gardn., 179, 184,
General Index
Anthemideae, 432 Schizaphis graminum, 485

Astereae, 433 Staphylococcus aureus, 487
Asteroideae, 432 Trirhabda spp., 488
benzofuranes, 432 abortifacient, 485
Biogenesis, cocklebur poisoning, 488
Ayapana, 386,417 Colorado potato beetle, 485
Brickel/ia, 389 hypoglycemia, 487
Chrysothamnus, 387 miracidal activity, 487
Conyza, 388, 418 molluscidal activity, 487
He/ichrysum, 389 mutagenesis, 488
Koanophyllon,387 sheep and cattle toxins, 487
Nidorella, 386, 418 surface resin, 486
Printzia, 388, 423 sweetener, 488
Relhania, 386, 420 13C-NMR Spectrometry
Trichogonia,426 beyeranes, 506
cassane, 388, 425 c1erodanes, 504
chrysolane, 387 labdanes, 505
c1eistanthane, 389, 427 pimaranes, 506
c1eistanthane, iso-, 389, 427 kauranes, 506
conyscabrane, 388, 423 Calenduleae, 433
ent-abietane, 389, 427 Chromenes, 432
ent-primarane, 427 Cichorioideae, 432
erythroxane, 389 Circular Dichroism, 495
normal-abietane, 388, 425 Cistaceae, 495
normal-pimarane, 388 Clerodanes
printzianes, 388 cis-ent-c1erodane, 495
relhaniane, 386 cis-normal-c1erodane, 494
rosane,426 trans-ent c1erodane, 493
sandaracopimarane, 425 trans-normal c1erodane, 496
solidagonane, 388 Compartmentation, 391
Biological Activity Cronquist, A., 432, 435
Candida albicans, 487 Cyclization, 385
Homeosoma electellum, 487 Distribution
Nicotiana glutinosa, 486 Baccharis, 435, 443, 470
Pectinophora gossypiella, 486 Brickellia, 434, 441, 457
638 General Index
Helianthus, 436, 452, 482 methyl chemical shift assignments,

Helichrysum, 435, 449, 480 498
A/ontanoa, 436, 456, 484 sandaracopimaranes, 506
Stevia, 434, 442, 462 Hardwickia pinnata, 493
Viguiera, 436, 452, 482 Heliantheae, 433
Elongatolides, 494 Kaurene synthetase CAB activity), 389
Eupatorieae, 432, 433 Lactuceae, 432
Ericaceae, 485 Lamiaceae, 485
Euphorbiaceae, 389, 485 Misra, R., 493
Geranylgeranyl pyrophosphate, 385, Phytol Rule, 385
437 Plathyterpenones, 494
Gibberellin, 386 "Rules" of Conformation, 500
Grindelanes, 386 Sesquiterpene Lactones, 432
I H-NMR Spectrometry Solidagolactones, 494
absolute stereochemistry, 497 Structure Description Codes, 3
3,4-epoxides, 501 Tori Equation, 503
C-6 substituents, 499 Trichomes, 391
C-7 substituents, 504 Velloziaceae, 389
C-12 substituents, 504 Vernonieae, 432, 436
C-17 substituents, 504 Wagenitz, G., 432, 438
C-19 substituents, 504 X-Ray Analysis, 505
cis-ent-clerodanes, 504 Ziircher Rules, 498
kolavanes, 494

Diterpenes of Flowering Plants

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Diterpenes of Flowering Plants

Uploaded by

Copyright:

Available Formats

Diterpenes of Flowering Plants

Diterpenes of Flowering Plants

Ferdinand Bohlmann Tom J. Mabry

Library of Congress Cataloging-in-Publication Data

Printed on acid-free paper

© 1990 by Springer-Verlag New York Inc.

Typeset by Technical Typesetting Incorporated, Baltimore, Maryland.

Chapter 1. Introduction ..................................... .

Chapter 2. Compound Names, Structures, and Sources ............ 3

11.1. Names of Reported Compounds . . . . . . . . . . . . . . . . . 3

Chapter 3. Biogenesis........................................ 385

111.1. ent- and Normal-Iabdanes ..................... 385

Chapter 4. Diterpene Distribution: Compositae ................... 431

IV.1. Subfamilial Distribution Patterns ................ 431

Chapter 5. Biological Activity of Diterpenes ..................... 485

V. 1. Introduction ............................. . . .. 485

Chapter 6. Diterpene Analysis with Emphasis on Clerodanes ....... 493

VI.l. Clerodanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 493

V1.3. Tricarbocyclics .............................. 505

Chapter 7. References ....................................... 551

Appendix Alphabetical Listing of Molecular Substituents

Compound Names, Structures, and

II. 1. Names of Reported Compounds

n.2. Structures of Reported Compounds

11.2.1. Structure Description Codes

II. Oxygen Functionalities

If no substituent is indicated for an available point of attachment at a skeletal

2.2.2. Examples of Molecular Descriptions

sequence-rule-preferred groups on this double bond, the hydroxymethylene

II. Bicyclic example: 14{:l-Carterothamnotriol-15-0-acetate

The skeleton immediately above this description of compound number 95

II.3. Plant Sources and References for Diterpenes

1101 Geranylascaridol, a-10,11H-10,11-dihydroxy-9-

II. Norma1-Bicarbocyc1ics and Derivatives

97 Brickellidiffusic acid angelate

107 Cativic acid, 2a-angeloyloxy-3a-hydroxy-(13Z)-13,

958 Labdan-1s-oic acid, 8a-hydroxy-

360 Labdane, (-)-7~,8a,ls-trihydroxy- [Gymnospermin]

135 Biformene, 3~-acetoxy-12,13E-

136 Biformene, 3-oxo-12,13E-

137 Communic acid

144 Abienol, 6~-hydroxy-12E-

145 Abienol, 7~-acetoxy-12E-

146 Abienol, 6~,7~-dihydroxy-12E-

147 Abienol, 6~,18-dihydroxy-12E-

148 Abienol, 7~-acetoxy-6~-hydroxy-12E-

149 Aristin-19-0-arachinate, l~-acetoxy-

150 Aristin-19-0-coumarate, l~-acetoxy-

151 Aristin-19-0-cis-coumarate, l~-acetoxy-

152 Labda-12(El,14-diene, 9a,19-dihydroxy-

157 Abienol, 7~-acetoxy-6~-hydroxy-12a-peroxiiso-

1140 Cordobic acid (7a,18-Dihydroxylabd-8(17)-en-oic acid]

1152 Gnaphala-13(16),14-diene, 8a-hydroxy-

17. Grinde lane

170 Grindelic acid, 6a-hydroxy-

173 Grindelic acid, 17-hydroxy- (Oxygrindelic acid]

176 Grindelic acid, 17-isobutyry1oxy-

192 Grindelic acid, 7a,8a-epoxy-7,8-dihydro-

1060 Grindelic acid-15-0-arabinoside

203 Carterochaetol, 16-hydroxy-

966 Labda-7,13-dien-15-acid-16-1actone, 17-oxo-

22. Normal-Labdane Spiroketal

218 Brickellidiffusic acid spiro ketal lactone, 2a-hydroxy-17,

[Published name, "3a,9~-dihydroxy-17-oxo-8~-H-ent-labda-13Z