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