The Alkaloids Vol.10

280 Pages·1981·13.52 MB·English

by  Royal Society of Chemistry (Great Britain)

The Alkaloids
Volume 10

A Specialist Periodical Report
The Alkaloids
Volume 10
A Review of the Literature Published
between July 1978 and June 1979
Senior Reporter
M. F. Grundon School of Physical Sciences, New University of
Ulster, Coleraine, Northern Ireland
Reporters
W. A. Ayer University of Alberta, Canada
K. W. Bentley University of Technology, Loughborough
(the late) J. Butterick University of West Virginia, U.S.A.
G. Fodor University of West Virginia, U.S.A.
D. M. Harrison New University of Ulster
R. B. Herbert University of Leeds
J. A. Lamberton C.S.I.R .O., Melbourne, Australia
J. R. Lewis University of Aberdeen
S. W. Page University of Georgia, U.S.A.
S. W. Pelletier University of Georgia, USA.
A. R. Pinder Clemson University, South Carolina, U.S.A.
D. J. Robins Glasgow University
J. E. Saxton University of Leeds
M. Shamma Pennsylvania State University, U.S.A.
The Royal Society of Chemistry
Burlington House, London WIV OBN
British Library Cataloguing in Publication Data
The alkaloids.-
(Royal Society of Chemistry. Specialist periodical reports).
VOl. 10
1. Alkaloids
I. Grundon, Michael Francis 11. Series
547l.72 QD421 70-616637
ISBN 0-85186-337-X
ISSN 0305-9707
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
Fore word
The flow of excellent alkaloid research proceeds unabated and for the tenth
successive year the contributors to this series have endeavoured to provide a
comprehensive review of the literature concerned with the chemistry of alkaloids.
We hope to maintain this unique feature of the publication, although the
escalating cost of production has resulted in the omission of much background
material and occasional more extensive reivews that were provided in earlier
volumes. The publication of this volume has been delayed for reasons beyond the
control of the contributors and the Royal Society of Chemistry.
With great regret I record the death of one of our authors, Dr. John Butterick.
October 1980 M. F. GRUNDON

Cont en ts
Chapter 1 Biosynthesis 1
By R. B. Herbert
1 Introduction 1
2 Piperidine, Pyridine, and Pyrrolidine Alkaloids 9
Securinine 10
Anabasine 10
Anatabine 11
Phomazarin 12
Tropane Alkaloids 12
Pyrrolizidine Alkaloids 13
Ricinine 14
Nicotine 14
3 Phenethylamine and Isoquinoline Alkaloids 15
Normacromerine 15
Peyote Alkaloids 15
Papaver Alkaloids 15
Coclaurine 15
Chelidonine 16
Bisbenzylisoquinoline Alkaloids 16
Ipecac Alkaloids 18
4 Alkaloids derived from Tryptophan 19
Terpenoid Indole Alkaloids 19
Pyrrolnitrin 23
Streptonigrin 23
Echinulin 24
Roquefortine 25
Ergot Alkaloids 26
5 Miscellaneous 27
Gliotoxin 27
Benzodiazepine Alkaloids 27
Quinoline Alkaloids 27
Phenazines 28
Actinomycin 28
P-Lactam Antibiotics 29
Ansamycins 29
vii
...
Vlll The Alkaloids
Chapter 2 Pyrrolidine, Piperidine, and Pyridine Alkaloids 30
ByA. R. Pinder
1 Pyrrolidine Alkaloids 30
Sceletium Alkaloids 31
2 Piperidine Alkaloids 31
Decahydroquinoline Alkaloids 36
Spiropiperidine Alkaloids 38
3 Pyridine Alkaloids 38
Chapter 3 Tropane Alkaloids 41
By G. Fodor and J. Butterick
1 New Alkaloids 41
2 Synthesis 42
3 Conformation 45
4 Photochemistry 46
5 Pharmacology 46
6 Analytical Aspects 47
Chapter 4 Pyrrolizidine Alkaloids 49
By D. J. Robins
1 Syntheses of the Necine Bases 49
2 Alkaloids of the Boraginaceae 52
3 Alkaloids of the Compositae 52
4 Alkaloids of the Elaeocarpaceae 55
5 Alkaloids of the Leguminosae 56
6 Alkaloids of the Scrophulariaceae 57
7 Pyrrolizidine Derivatives in the Lepidoptera 57
8 General Studies 58
9 Pharmacological and Biological Studies 60
Chapter 5 lndolizidine Alkaloids 63
By J. A. Lamberton
1 Elaeocarpus Alkaloids 63
2 Xpomoea Alkaloids 63