Aliphatic and Related Natural Product Chemistry Vol. 3

380 Pages·1983·14.786 MB·English

by  F D Gunstone

Aliphatic and Related Natural
Product Chemistry
Volume 3

A Specialist Periodical Report
Aliphatic and Related Natural
Product Chemistry
Volume 3
A Review of the Literature published
during 1980 and 1981
Senior Reporter
F. D. Gunstone Department of Chemistry,
University of St Andrews
Reporters
R. Baker University of Southampton
J. W. S. Bradshaw University ofS outhampton
W. W. Christie The Hannah Research Institute, Ayr
D. H. Grayson Trinity College, Dublin
R. H. Green Glaxo Group Research, Greenford, Middlesex
R. C. F. Jones University of Nottingham
P. F. Lambeth Glaxo Group Research, Greenford, Middlesex
R. F. Newton Glaxo Group Research, Ware, Hefts
S. M. Roberts Glaxo Group Research, Greenford, Middlesex
C. M. Scrimgeour University of Dundee
The Royal Society of Chemistry
Burlington House, London WIV OBN
ISBN 0-8.5 186-662-X
ISSN 0142-7318
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
Printed in Great Britain
by Whitstable Litho Ltd. Whitstable, Kent
Foreword
This volume is the first in any of the series of Specialist Periodical
Reports to be produced from the authors' camera-ready typescripts.
We would choose that volumes such as this were typeset, because of
the compactness of such books relative to those prepared from
camera-ready copy, but, as indicated by the term Specialist, books
such as this can only ever serve a very limited readership. The
high costs of technical typesetting must therefore be shared amongst
a small number of books sold. At a time when many individuals and
librarians must critically scrutinise the list of bcoks that they
would wish to buy and then consider how much of that list they can
afford, the avoidance of the cost of typesetting will, we hope,
allow the information in these Reports to reach as wide an audience
as is practical.
Alongside the constraints placed on the budgets of many librarians,
many organisations have had to restrict or reduce the secretarial
help available to prospective authors. Several of the authors who
contributed to this volume have had to overcome such handicaps, even
to the extent of producing the typescripts themselves. Without
their co-operation, we would not have produced this volume.
The Royal Society of Chemistry B 3 Starkeg
October 1982 (Editor, Booksj

Con tent s
Chapter 1 Natural Acetylenic and Olefinic Compounds 1
By C.M.Scrimgeour
1 Introduction 1
2 Natural Acetylenic Compounds 1
2.1 Introduction 1
2.2 New Polyacetylenic Compounds from
Terrestrial Plants 1
2.3 Known Polyacetylenic Compounds from
Terrestrial Plants 8
2.4 Acetylenic Compounds of Marine Origin 9
2.5 Biosynthesis of Acetylenic Compounds 12
2.6 Physiological Role of Polyacetylenic Compounds 14
3 Natural Olefinic Compounds 17
3.1 Isolation 17
3.2 Synthesis 18
References 23
Chapter 2 Acyclic Terpenoids 26
By D.H.Grayson
1 Introduction 26
2 Isoprene Chemistry 26
3 Irregular Systems 31
4 2,6-Dimethyloctane Group 33
4.1 Ocimenes 33
4.2 Myrcenes 34
4.3 Citronellyl Derivatives 35
4.4 Linalyl Derivatives 38
4.5 Geranyl and Neryl Derivatives 42
5 Sesquiterpenes 54
6 Diterpenes 59
7 Squalene 61
8 Polyterpenoids 61
References 62
...
Vlll Aliphatic and Related Natural Product Chemistry
Chapter 3 Insect Pheromones and Related Natural Products 66
By R. Baker and J.W.S. Bradshaw
1 Introduction 66
2 Pheromones 66
2.1 Sex Pheromones of Lepidoptera 66
2.2 Aggregation Pheromones of Coleoptera 71
2.3 Sex Pheromones of Diptera 71
2.4 Pheromones of Hymenoptera - Bees, Wasps, and Ants 72
2.5 Other Pheromones 74
3 Defensive Secretions 74
4 Other Exocrine Products 78
5 Biosynthesis and Biotransformation 78
6 Separation and Structure-Elucidation Techniques 80
7 Synthetic Studies 81
7.1 Mono-unsaturated Derivatives 81
7.2 Di-unsaturated Derivatives 83
7.3 Tri-unsaturated Derivatives 87
7.4 Ketones, Alcohols, and Acetates 89
7.5 Epoxides 93
7.6 Lactones 93
7.7 Ketals 96
7.8 Spiroketals 98
References 101
Chapter 4 Prostaglandins and Leukotrienes 107
By R.F. Newton, S.M. Roberts, R.H. Green, and P.F. Lambeth
1 Introduction 107
2 Synthesis of PGs A-F 108
2.1 Routes via the Corey Lactone 108
2.2 Glaxo Syntheses 113
2.3 Conjugate Addition to 4-Substituted Cyclopentenones 118
2.4 Miscellaneous Procedures 121
3 Reactions of PGs A-F 123
4 Synthesis of Analogues of PGs A-F 126
4.1 Deoxyprostaglandins 126
4.2 Fluoroprostaglandins 133
4.3 Azaprostaglandins 135
4.4 Oxa- and Thia-prostaglandins 140
4.5 Miscellaneous Analogues 141
4.5.1 Cyclopentane-ring Variants 141
4.5.2 Lower Side-chain Variants 145