Terpenoids and Steroids, Volume 12 PDF
Preview Terpenoids and Steroids, Volume 12
Terpenoids and Steroids Volume 12 A Specialist Periodical Report ~~ Terpenoids and Steroids Volume 12 A Review of the Literature Published between September 1980 and August 1981 Seni or Reporter . J R. Hanson ScboolofMolecular Sciences, University of Sussex Reporters D. V. Banthorpe University College, London R. B. Boar Chelsea College, London S. A. Branch University College, London G. Britton University of Liverpool 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 W1 V OBN ISBN 0-85186356-6 ISSN 0300-5992 Copyright 0 1983 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 Typeset by Bath Typesetting Ltd., Bath and printed by Adlard and Son Ltd., Bartholomew Press, Dorking Made in Great Britain Introduction This is the last of the ‘Terpenoids and Steroids’ Specialist Periodical Reports. This title along with ‘Aliphatic and Related Natural Product Chemistry’, ‘The Alkaloids’ and ‘Biosynthesis’, has been subsumed into a review journal entitled Natural Product Reports. Whilst maintaining the thoroughness of coverage which has characterized the individual reports, the new journal will aim to avoid overlap and, because it will appear more frequently, the time delay between the completion of a chapter and public- ation which arises in the present reports from the irregular completion of manuscripts. The title of the new journal allows for a greater flexibility in scope and it will contain reports, particularly on techniques, which cut across the traditional boundaries between the individual groups of natural product. I should like to thank all those contributors who have made the present series a success and I wish the chairman of the Editorial Board, Professor Pattenden, good luck in this new venture. J. R. HANSON Contents Part / Terpenoids Chapter 1 Monoterpenoids 3 By D. V. Banthorpe and S. A. Branch 1 Introduction 3 2 Physical Methods: Chirality 4 Spectral and Other Physical Data 4 Chirality 7 3 General Synthetic Methods 8 4 The Acyclic Class 14 Occurrence 14 Synthesis of the C,, Skeleton 15 Reactions of 3,7-Dimethyloctadienes and their Derivatives 19 Reactions with Metal Complexes 22 Oxidation and Reduction 23 Cyclizations, Isomerizations, etc. 25 5 Tetramethylcyclohexanesa nd Related Compounds 29 6 The Menthane Class 32 General 32 Formation of the Menthane Skeleton 33 Oxidation, Reduction, and Related Reactions 35 Alkylation, Homologation, and Related Processes 39 General Reactions 41 7 The Camphane Class 44 Occurrence; Synthesis of the Skeleton 44 Oxidation-Reduction 45 General Reactions 45 8 The Isocamphane Class 47 9 The Pinane Class 48 Occurrence 48 Rearrangement, Oxidation, Reduction, Simple Functionalizations 48 Ring-opening 50 Homologation, More Complicated Functionalization 51 Norpinane Derivatives 52 vii viii Terpenoids and Steroids 10 The Fenchane Class 53 11 The Thujane Class 53 Occurrence 53 Reactions 54 12 The Carane Class 55 Reactions Preserving the Carane Skeleton 55 Formation of Bicycle[ 3.1 .O]hexane Derivatives 56 Formation of Menthane or Cyclopropane Derivatives 56 13 The Cyclopentane (‘Iridane’) Class 57 Occurrence 57 Synthesis and Reactions 60 14 The Irregular Classes 61 Occurrence 62 Syntheses and Reactions 62 15 Cannabinoids and Other Phenolic Monoterpenoids 65 Cannabinoids 65 Thymol Derivatives 66 Occurrence 66 Reactions 67 16 Biogenesis, Ch emotaxonomy, Biological Applications 67 Labelling Patterns; Cell-free Extracts 68 Tissue Cultures, Microbial Transformations 72 Chemotaxonomy 73 Metabolism, Biological Activity, Miscellaneous 73 Chapter 2 Sesquiterpenoids 75 By J. S. Roberts 1 Farnesane 75 2 Mono- and Bi-cyclofarnesane 78 3 Bisabolane 88 4 Sesquicamphane, Sesquipinane 89 5 Cuparane, Herbertane, Lame, Trichothecane 92 6 Chamigrane, Widdrane 99 7 Acorane, Carotane, Cedrane, Zizaane 100 8 Cadinane, Cubebane, Oplopanane, Picrotoxane, Sativane, Copacamphane 106 9 Himachalane, Longifolane, Longipinane 114 10 Caryophyllane, Humulane, and Related Sesquiterpenoids 115 11 Germacrane 140
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