The Alkaloids: A Review of Chemical Literature: v. 8 (Specialist Periodical Reports)

290 Pages·1978·18.72 MB·English

by  M F Grundon

A Specialist Periodical Report
The Alkaloids
Volume 8
A Review of the Literature Published
between July 1976 and June 1977
Senior Rep0 rte r
M. F. Grundon, School of Physical Sciences, New University of
Ulster, Coler ai ne , North ern Ire land
Reporters
W. A. Ayer, University of Alberta, Canada
K. W. Bentley, University of Technology, Loughborough
S. 0. de Silva, University of Waterloo, Ontario, Canada
D. M. Harrison, New University of Ulster
R. B. Herbert, University of Leeds
J. A. Lamberton, C.S.I.R.O., Melbourne, Australia
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.
J. N. Reed, University of Waterloo, Ontario, Canada
D. J. Robins, Glasgow University
J. E. Saxton, University of Leeds
M. Shamma, Pennsylvania State University, U.S.A.
V. A. Snieckus, University of Waterloo, Ontario, Canada
The Chemical Society
Burlington House, London, WIV OBN
British Library Cataloguing in Publication Data
The alkaloids.
Vol. 8. - (Chemical Society. Specialist periodical reports).
1. Alkaloids
I. Grundon, Michael Francis 11. Series
547l.72 QD421 70-616637
ISBN 0-85186-327-2
ISSN 0305-9707
Copyright @ 1978
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 intention of the eighth volume of The Alkaloids was once again to provide a
comprehensive annual survey of the alkaloid literature. It has not been possible,
however, to include chapters on the Tropane Alkaloids and on Miscellaneous
Alkaloids, and certain aspects of the chemistry of isoquinoline alkaloids have been
omitted; we expect to remedy these deficiencies by including a two-year coverage
in Volume 9.
A number of our regular authors are not participating this year, and I would like
to express my appreciation to Drs. Crout and McCorkindale for their contribution
to Volumes 6 and 7 and in particular to Drs. Goutarel and Khuong-Huu for
reviewing steroidal alkaloids of the Apocynaceae and Buxaceae since the
inauguration of this series of Reports in 1971. In this Volume, all steroidal
alkaloids are included in Chapter 14.
May I remind alkaloid chemists that comments on these Reports are welcome
and that it is very helpful for authors to receive reprints of articles published in
journals that are not generally accessible.
The untimely death of Professor S. M. Kupchan is referred to in Chapter 8. His
important contributions to the chemistry of isoquinoline and steroidal alkaloids and
his interest in anti-tumour alkaloids have been a regular feature of these reports.
April 1978 M. F. GRUNDON

Cont en ts
Chapter 1 Biosynthesis 1
By R. B. Herbert
1
1 Introduction
2 Piperidine, Pyridine, and Pyrrolidine Alkaloids
Dioscorine
Anatabine
Lupin Alkaloids
Securinine
Proferrorosamine A
Nicotine
Phenanthroindolizidine Alkaloids
Tropane Alkaloids
3 Isoquinoline Alkaloids 8
Protostephanine and Hasubanonine 8
Erythrina Alkaloids 10
Cephalotaxus Alkaloids 12
Protoberberine Alkaloids 14
Papaverine 19
Aporphine Alkaloids 19
4 Amaryllidaceae and Mesembrine Alkaloids 19
Amaryllidaceae Alkaloids 19
Mesembrine Alkaloids 21
5 Alkaloids Derived from Tryptophan 22
Grarnine 22
Indolmycin 23
Anthramycin, Pyrrolnitrin, and Tomaymycin 24
Benzodiazepine Bases 26
Cyclopiazonic Acid 27
Ergot Alkaloids 27
Terpenoid Indole Alkaloids 27
6 Steroidal Alkaloids 28
7 Miscellaneous 30
Nybomycin and Geldanomycin 30
Shihunine 33
Phenazines 33
V
vi The Alkaloids
Mycelianamide 35
&Lactam Antibiotics 35
Prodigiosin 36
Chapter 2 Pvrrolidine, Piperidine, and Pyridine Alkaloids 37
ByA. R. Pinder
1 Pyrrolidine Alkaloids 37
Dendrobium Alkaloids 37
Sceletium Alkaloids 39
2 Piperidine Alkaloids 40
Decahydroquinoline Alkaloids 43
3 Pyridine Alkaloids 44
Chapter 3 Pyrrolizidine Alkaloids 47
By D. J. Robins
1 Syntheses and Reactions of the Necine Bases 47
2 Alkaloids of the Graminae 49
3 Alkaloids of the Boraginaceae 49
4 Alkaloids of the Leguminosae 50
5 Alkaloids of the Compositae 51
6 Pyrrolizidine Derivatives in the Lepidoptera 57
7 General Studies 58
8 Pharmacological and Biological Studies 59
Chapter 4 lndolizidine Alkaloids 62
By J. A. Lamberton
1 Alkaloids of Tylophora and Related Species 62
2 Gephyrotoxin 63
3 Elaeocarpus Alkaloids 63
4 Trail Pheromone of the Pharaoh’s Ant 63
5 General Syntheses of Indoliidines 65
Chapter 5 Quinolizidine Alkaloids 66
By M. F. Grundon
1 Lupinine-Lupanine-Sparteine-Matrine Group and the
Ormosia Alkaloids 66
Occurrence 66
Cont ents vii
Lupinine Group 66
Lupanine-Sparteine Group 68
Matrine Group 69
Ormosia Group 70
2 Sesquiterpenoid Alkaloids 70
3 Lythraceae Alkaloids 74
Chapter 6 Quinoline, Quinazoline, and Acridone Alkaloids 77
By M. F. Grundon
1 Quinoline Alkaloids 77
Isolation and Spectroscopic Studies 77
Non-hemiterpenoid Quinolines 80
Furoquinoline Alkaloids 81
3-Prenylquinoline Alkaloids and Related Compounds 81
2 Quinazoline Alkaloids 83
3 Acridone Alkaloids 84
Chapter 7 P-Phenethylamines and the lsoquinoline Alkaloids 87
By K. W. Bentley
1 P-Phenethylamines 87
2 Simple Isoquinoline Alkaloids 87
3 Benzylisoquinoline Alkaloids 88
4 Phenethylisoquinoline Alkaloids 93
5 Pavines and Isopavines 94
6 Bisbenzylisoquinoline Alkaloids 94
7 Protoberberines 98
8 Protopines 107
9 Phthalide-isoquinoline Alkaloids 107
10 Spirobenzylisoquinoline Alkaloids 109
11 Rhoeadine Alkaloids 110
12 Morphine Alkaloids 111
Chapter 8 Aporphinoid Alkaloids 122
By M. Shamma
1 Introduction 122
2 Proaporphines 122
...
Vlll The Alkaloids
3 Aporphines 123
4 Aporphine-Benzylisoquinoline Dimers 132
5 Oxoaporphines 133
6 Phenanthrenes, Taspine, 4,5-Dioxoaporphines,
Aristolochic Acids, and Aristolactams 134
7 Azafluoranthenes and Diazafluoranthenes 135
Chapter 9 Amaryllidaceae and Related Alkaloids 137
By J. N. Reed and V. A. Snieckus
Chapter 10 Erythrina and Related Alkaloids 144
By S. 0. de Silva and V. A. Snieckus
Chapter 11 lndole Alkaloids 149
By J. E. Saxton
1 Introduction 149
2 Simple Alkaloids 149
Non-tryptamines 149
Non-isoprenoid Tryptamines 154
3 Isoprenoid Tryptamine and Tryptophan Alkaloids 156
Mould Metabolites 156
Ergot Alkaloids 158
Monoterpenoid Alkaloids 164
Corynantheine-Heteroyohimbine-Yohimbine Group,
and Related Oxindoles 164
Sarpagine-Ajmaline-Picraline Group 182
Strychnine-Akuammicine-Condylocarpine-Ellipticine-
Uleine Group 188
Aspidospermine-Aspidofractine-Eburnamine Group 191
Ibogamine-Catharanthine-Cleavamine Group 198
4 Bis-indole Alkaloids 201
5 Biogenetically Related Quinoline Alkaloids 214
Chapter 12 L ycopodium Alkaloids 216
By W. A. A yer
Chapter 13 Diterpenoid Alkaloids 219
By S. W. Pelletier and S. W. Page
1 Introduction 219