The Alkaloids Vol.12

336 Pages·1982·19.6 MB·English

The Alkaloids
Volume 12

A Specialist Periodical Report
The Alkaloids
Volume 12
A Review of the Literature Published
between July 1980 and June 1981
Senior Reporter
M. F. Grundon School of Physical Sciences, New University of
Ulster, Coleraine, Northern Ireland
Reporters
K. W. Bentley University of Technology, Loughborough
A. S. Chawla University College, Cardiff
R. Dharanipragada University of West Virginia, U.S.A,
G. Fodor University of West Virginia, U.S.A.
H. Guinaudeau University of Limoges, France
D. M. Harrison New University of Ulster
R. B. Herbert University of Leeds
A. H. Jackson University College, Cardiff
J. A. Lamberton C.S.I.R .O., Melbourne, Australia
J. R. Lewis University of A berdeen
S. W. Page University of Georgia, U.S.A.
S. W. Pelletier University of Georgia, U.S.A.
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 W1V OBN
ISBN 0-85186-357-4
ISSN 0305-9707
Copyright 0 1982
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
Spottiswoode Ballantyne Ltd.,
Colchester and London
Foreword
The whole of the alkaloid literature is reviewed for the year with the exception of
Lycopodium Alkaloids, which will be given a two-year coverage in Volume 13. As
in previous volumes of the series we aim to include all references to the isolation,
structure, chemistry, synthesis, and biosynthesis of alkaloids and to provide an
adequate account of biological properties. The annual comprehensive treatment is
unique in the alkaloids literature and has received much support. Rising costs,
however, have put the future of the series in doubt and we are experimenting with
cheaper methods of production; alternative means of producing chemical structures
were used in Volume 10 (Chapters 6, 7 and 10) and in this Volume (Chapters
1, 6, 7, 10 and 14), I believe without significant reduction in quality, and Volume 13
will be published from camera-ready copy. These changes place an added burden
on our authors and I would like to express my gratitude for their continuing
commitment to the principles of this series and for their willingness to take part in
new production techniques.
September 1982 M. F. GRUNDON

Contents
Chapter 1 B iosynt he sis 1
By R. B. Herbert
1 Pyrrolidine and Piperidine Alkaloids 1
Simple Pyrrolidine Alkaloids 1
Phenanthroindolizidine Alkaloids 4
Pyrrolizidine Alkaloids 4
Lysine 6
Quinolizidine Alkaloids 7
2 Isoquinoline Alkaloids 9
Papaver Alkaloids 9
Aporphine and Berberine Alkaloids 10
BisbenzylisoquinolineA lkaloids 11
3 Alkaloids Derived from Tryptophan 14
P-Carboline Alkaloids 14
Terpenoid Indole Alkaloids 14
Ergot Alkaloids 16
P yrrolnitrin 18
Indolmy cin 20
Penitrems 20
Anthramycin 21
4 Miscellaneous 21
Ansamycins, Mitomycins, and Pactamycin 21
0-Lactam Antibiotics 25
Aranotins and Sirodesmin 28
Phenazines 29
Cytochalasins 31
C ycloheximide 31
Steroidal Alkaloids 33
Betalains 33
Capsaicin 33
Chapter 2 Pyrrolidine, Piperidine, and Pyridine Alkaloids 35
ByA. R. Pinder
1 Pyrrolidine Alkaloids 35
Sceletium Alkaloids 38
Dendrobium Alkaloids 38
viii The Alkaloids
2 Piperidine Alkaloids 38
Decahydroquinoline Alkaloids 41
Spiropiperidine Alkaloids 42
Bispiperidine Alkaloids 42
3 Pyridine Alkaloids 42
Chapter 3 Tropane Alkaloids 45
By G. Fodor and R. Dharanipragada
1 Structure of New Alkaloids 45
2 Synthesis and Reactions 48
3 Pharmacology 51
4 Analytical Aspects 52
Chapter 4 Pyrrolizidine Alkaloids 54
By D. J. Robins
1 Syntheses of Necine Bases 54
2 Synthesis of Neck Acids 59
3 Synthesis of Macrocyclic Diesters 59
4 Alkaloids of the Boraginaceae 61
5 Alkaloids of the Compositae 62
Eupatorieae Tribe 62
Senecioneae Tribe 62
6 Alkaloids of the Gramineae 64
7 Alkaloids of the Leguminosae 64
8 Alkaloids from Animals 65
9 General Studies 66
10 Pharmacological and Biological Studies 67
Chapter 5 In dolizidine Alkaloids 69
By J. A. Lamberton
1 Castanospermum Alkaloids 69
2 Prosopis Alkaloids 69
3 Elaeocarpus Alkaloids 69
4 Dendrobates Alkaloids 71
5 Phenanthroindolizidines 72