Alkaloids (v. 9)

290 Pages·1979·16.76 MB·English

by  Royal Society Of Chemistry

The Alkaloids
Volume 9

A Specialist Periodical Report
The Alkaloids
Volume 9
A Review of the Literature Published
between July 1977 and June 1978
Senior Reporter
M. F. Grundon School of Physical Sciences, New University of
Ulster, Coleraine, Northern Ireland
Reporters
K. W. Bentley University of Techology , Loughborough
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
A. H. Jackson University College, Cardiff
J. A. Lamberton C.S.I.R.O.,M elbourne, Australia
J. R. Lewis University of Aberdeen
S. W.P age 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 Chemical Society
Burlington House, London, WIV OBN
British Library Cataloguing in Publication Data
The alkaloids.-
(Chemical Society. Specialist periodical reports).
Vol. 9
1. Alkaloids
I. Grundon, Michael Francis
547l.72 QD421 70-616637
ISBN 0-85 186-660-3
ISSN 0305-9707
Copyright @ 1979
The Chemical Society
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 Chemical Society
Set in Times on Linotron and printed offset by
J. W. Arrowsmith Ltd, Bristol, England
Made in Great Britain
Fore word
The policy adopted in this ninth volume of The Alkaloids is once again to furnish a
comprehensive annual survey of the alkaloid literature. As a result of unavoidable
omissions in the eighth volume, a two-year coverage is provided of tropane
alkaloids and, within the isoquinoline group (Chapter 8), of the chemistry of
emetine and related bases, dibenzopyrrocolines, benzophenanthridines, and
colchicine. The chapter on Miscellaneous Alkaloids also surveys the literature of
the period July 1976-June 1978; purines are no longer included.
Dr. V. A. Snieckus, one of our most regular authors, is not taking part this year,
and I would like to draw particular attention to his substantial and invaluable
contributions to the preceding eight volumes.
Dr. R. H. F. Manske, who died in late 1977 as a result of a motor car accident,
was a life-long alkaloid chemist and founder editor of the review series ‘The
Alkaloids’; a tribute to Dr. Manske and his work is included in Volume XVII of
the series.
July 1979 M. F. GRUNDON

Cont en ts
Chapter I Biosyn thesis 1
By R. B. Herbert
1 Introduction 1
2 Piperidine, Pyridine, and Pyrrolidine Alkaloids 1
Dioscorine 1
Coniine 2
Quinolizidine Alkaloids 2
Pyrindicin 3
Tenellin 3
Tropane Alkaloids 3
Pyrrolizidine Alkaloids 4
Phenanthroindolizidine Alkaloids 5
Nicotine 7
3 Phenethylamine and Isoquinoline Alkaloids 7
Normacromerine 7
Reticuline 8
Morphinan Alkaloids 8
Bisbenzylisoquinoline Alkaloids 11
Protoberberine and Related Alkaloids 14
Aporphine Alkaloids 14
Erythrina Alkaloids 16
4 Mesembrine Alkaloids 16
5 Alkaloids Derived from Tryptophan 18
Terpenoid Indole Alkaloids 18
Echinulin 24
Streptonigrin 24
Actinomycin 26
Ergot A1 kaloids 26
6 Steroidal Alkaloids 27
7 Miscellaneous 28
Phenazines 28
Ch loramp henicol 31
Prodiginines 32
/3 -Lactam Antibiotics 32
Nocardicins 33
Rif amycins 34
vii
...
Vlll The Alkaloids
Chapter 2 Pyrrolidine, Piperidine, and Pyridine Alkaloids 35
By A. R. Pinder
1 Pyrrolidine Alkaloids 35
Dendrobium Alkaloids 36
Sceletium Alkaloids 36
2 Piperidine Alkaloids 36
Spiropiperidine Alkaloids 40
Decahydroquinoline Alkaloids 41
3 Pyridine Alkaloids 41
Celastraceae Alkaloids 44
Chapter 3 Tropane Alkaloids 46
By G. Fodor and J. Butterick
1 Occurrence, and Structures of New Alkaloids 46
Three-dimensional Structure 47
2 Synthesis 48
3 Pharmacology 52
4 Analytical Aspects 53
Chapter 4 Pyrrolizidine Alkaloids 55
By D. J. Robins
1 Syntheses of the Necine Bases 55
2 Alkaloids of the Boraginaceae 58
3 Alkaloids of the Compositae 59
4 Alkaloids of the Leguminosae 62
5 Alkaloids of the Ranunculaceae 63
6 Alkaloids in Animals 63
7 General Studies 63
8 Pharmacological and Biological Studies 65
Chapter 5 lndolizidine Alkaloids 67
By J. A. Lamberton
1 Ipomoea Alkaloids 67
2 Tylophora Alkaloids 67
3 Elaeocarpus Alkaloids 67
4 Slaframine 67