A review of the literature published between September 1978 and August 1979

300 Pages·1981·14.897 MB·English

by  J R Hanson, Royal Society of Chemistry

Terpenoids and Steroids
Volume 10

A Specialist Periodical Report
Terpenoids and Steroids
Volume 10
A Review of the Literature Published
between September 1978 and August 1979
Senior Reporter
J. R. Hanson, School of Molecular Sciences, University of Sussex
Reporters
G. Britton, University of Liverpool
J. D. Connolly. University of Glasgow
D. N. Kirk, Westfield College, London
B. A. Marples, University of Technology, Loughborough
J. S. Roberts, University of Stirling
The Royal Society of Chemistry
Burlington House, London WIV OBN
British Library Cataloguing in Publication Data
Terpenoids and steroids.
(The Royal Society of Chemistry. Specialist periodical reports).
VOl. 10
1. Terpenes 2. Steroids
I. Hanson, James Ralph 11. Series
547’.71 QD416 74-615720
ISBN 0-85186-336-1
ISSN 0300-5992
Copyright @ 1981
The Royal Society of Chemistry
All Rights Reserved
No part of this book may be reproduced or transmitted
in any form or by any means-graphic, electronic,
including photocopying, recording, taping or
information storage and retrieval systems-without
written permission from The Royal Society of Chemistry
Set in Times on Linotron and printed offset by
J. W. Arrowsmith Ltd., Bristol, England
Made in Great Britain
In trod u c tion
The intention of this volume is to provide an annual survey of the terpenoid and
steroid literature. In the past year a fascinating variety of terpenoid structures has
been described, particularly from marine and insect sources. The value of
high-field 'H n.m.r. and I3C n.m.r. data in structural elucidation is apparent
although it has, inevitably, led to a decrease in the amount of new natural product
chemistry which has been described. In some cases the spectroscopic elucidation
of a structure has left the absolute stereochemistry undetermined or merely
assigned by analogy. Since there are a number of examples where both enan-
tiomers of a structure are known, this is a dangerous omission. There are now a
number of areas amongst both the sesquiterpenoids and the diterpenoids where
there is a clear need for an unambiguous correlation with known structures of
proven absolute stereochemistry.
The format of these Reports has remained relatively constant to fadilitate the
location of subject matter. These chapters cover the period from September 1978
to August 1979. Unfortunately it has not been possible to include the customary
chapter on the monoterpenoids. We hope to remedy this deficiency by including
the chapter in the next volume. Whilst there has been some overlap with the
companion volumes on the Alkaloids, on Aliphatic and Related Natural Product
Chemistry, and on Biosynthesis, we have endeavoured to keep this to a minimum,.
J. R. HANSON
V

Cont en ts
Part I Terpenoids
Chapter 1 Sesquiterpenoids 3
By J. S. Roberts
1 Introduction 3
2 Farnesane 3
3 Bicyclofarnesane 5
4 Bisabolane, Sesquicarane 11
5 Sesquipinane, Sesquicamphane 17
6 Cuparane, Trichothecane 20
7 Chamigrane, Widdrane, Thujopsane, 21
8 Acorane, Cedrane, Carotane, Zizaane 25
9 Cadinane, Muurolane, Copaane, Cyclosesquifenchane,
Sativane, Copacamphane, Picrotaxane 28
10 Himachalane, Longipinane, Longifolane 34
11 Caryophyllane, Humulane, Africane, Illudalane,
Protoilludane, Hirsutane, Vellerane, Pentalane,
Senoxydane 38
12 Germacrane 51
13 Elemane 65
14 Eudesmane 69
15 Vetispirane 75
16 Eremophilane, Nootkatane, Ishwarane 80
17 Guaiane, Pseudoguaiane, Seychellane, Patchoulane 87
18 Aromadendrane, Maaliane 99
19 Miscellaneous 101
vii
Vlll '1 erpenoids and Steroids
Chapter 2 Diterpenoids 106
By J. R. Hanson
1 Introduction 106
2 Acyclic and Related Diterpenoids 106
3 Bicyclic Diterpenoids 107
Labdanes 107
Clerodanes 110
4 Tricyclic Diterpenoids 114
Naturally Occurring Substances 114
Chemistry of the Tricyclic Diterpenoids 116
5 Tetra- and Penta-cyclic Diterpenoids 117
Kaurenoid Diterpenoids 117
Beyerene Diterpenoids 119
Atiserene Diterpenoids 120
Trachylobane Diterpenoids 120
Gibberellins 121
Grayanotoxins 123
Diterpenoid Alkaloids 123
6 Macrocyclic Diterpenoids and their Cyclization Products 124
7 Miscellaneous Diterpenoids 126
8 Diterpenoid Total Synthesis 131
Chapter 3 Triterpenoids 135
By J. D. Connolly
1 Squalene group 135
2 Fusidane-Lanostane Group 137
3 Dammarane-Euphane Group 142
Tetranortriterpenoids 144
Pentanortriterpenoids 151
Quassinoids 152
4 Shionane-Baccharane Group 153
5 Lupane Group 154
6 Oleanane Group 155
7 Ursane Group 160
8 Hopane Group 162
9 Stictane Group 163