The Alkaloids Vol.07

346 Pages·1977·23.94 MB·English

A Specialist Periodical Report
~ ~ ~~
The Alkaloids
Volume 7
A Review of the Literature Published
between July 1975 and June 1976
Senior Reporter
M. F. Grundon, School of Physical Sciences, New University of
Ulster, Coleraine, Northern Ireland
Reporters
D. H. G. Crout, University of Exeter
G. Fodor, West Virginia University, U.S .A .
R. Goutarel, Centre National de la Recherche Scientifique, France
D. M. Harrison, New University of Ulster
R. B. Herbert, University of Leeds
F. Khuong-Huu, Centre National de la Recherche Scientifique, France
J. A. Lamberton, C.S.I.R.O., Victoria, Australia
N. J. McCorkindale, University of Glasgow
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
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
ISBN: 0 85186 317 5
ISSN: 0305-9707
Library of Congress Catalog No. 70-616637
Copyright @ 1977
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 seventh volume of The Alkaloids follows the policy and format adopted in
preyious volumes. Most sections are concerned with literature published during July
1975-June 1976, but the three Chapters on Amaryllidaceae and Related
Alkaloids, Erythrina and Related Alkaloids, and Miscellaneous Alkaloids cover
the two-year period up to June 1976.
The dedication of the Chapter on Indole Alkaloids to Professor R. B. Woodward
acknowledgesh is contributions to alkaloid chemistry during more than thirty years.
My editorial work has been made so much easier by the ready co-operation and
understanding of the contributors and it is a pleasure to record my appreciation.
June 1976 M. F. GRUNDON
...
111

Cont ents
Chapter 1 Biosynthesis 1
By R. B. Herbert
1 Introduction 1
2 Piperidine, Pyridine, and Pyrrolidine Alkaloids 2
Securinine 2
Ly copodine 3
Pinidine and Coniine 4
Coccinelline 5
Tropane Alkaloids 5
Pyrrolizidine A1 kaloids 8
Lythraceae Alkaloids 9
Tenellin 9
3 Isoquinoline Alkaloids 10
Schelhammeridine 10
Reticuline 10
Papaverine 12
Stylopine, Chelidonine, and Related Alkaloids 12
Narcotine 16
4 Alkaloids Derived from Tryptophan 16
Indolmycin 16
Cyclopiazonic Acid 18
Echinulin 19
Ergot Alkaloids 20
Camptot hecin 21
Terpenoid Indole Alkaloids 22
5 Miscellaneous Bases of Aromatic Origin 23
Mesembrine Alkaloids 23
Gliotoxin 24
Benzodiazepine Bases 24
Anthramycin and Related Antibiotics 25
Phenazines 27
Dolichotheline 28
Cytochalasins 29
6 Miscellaneous Bases of Aliphatic Origin 30
p -Lactam Antibiotics 30
Streptovaricins and Mitomycins 32
Azetidine-2-carboxylic Acid 32
Steroidal and Terpenoid Alkaloids 32
V
vi The Alkaloids
Chapter 2 Pyrrolidine, Piperidine, and Pyridine Alkaloids 35
By A. R. Pinder
1 Pyrrolidine Alkaloids 35
Dendrobium Alkaloids 36
2 Piperidine Alkaloids 37
Spiropiperidine Alkaloids 40
Decahydroquinoline Alkaloids 41
3 Pyridine Alkaloids 41
Chapter 3 Tropane Alkaloids 47
By G. Fodor
1 Occurrence and Isolation of New Alkaloids 47
2 Synthetic, Chemical, and Pharmacological Studies 50
3 Analytical 52
Chapter 4 The Pyrrolizidine Alkaloids 54
By D. H. G. Crout
1 The Neane Bases 54
2 The Neac Acids 55
3 The Ester Alkaloids 56
4 General Studies 61
5 Pharmacological and Biological Studies 64
Chapter 5 lndolizidine Alkaloids 66
By J. A. Lamberton
1 Tylophoru Alkaloids 66
2 Scent-gland Constituent of Canadian Beaver 68
Chapter 6 The Quinolizidine Alkaloids 69
By M. F. Grundon
1 The Lupinine-Lupanine-Sparteine-Matrine Group and the
Ormosiu Alkaloids 69
Occurrence 69
Lupinine Group 71
Lupanine-Sparteine Group 72
Matrine Group 74
Ormosia Group 74
2 Sesquiterpenoid Alkaloids from Nuphur Species 75
Contents vii
3 Lythruceue Alkaloids 77
4 9CAzaphenalene Alkaloids 78
Chapter 7 Quinoline and Acridone Alkaloids 81
By M. F. Grundon
1 Quinoline Alkaloids 81
Non- hemi terpenoid Qui nolines 8i
Furoquinoline Alkaloids 82
Heliparvifoline 82
Haplatine, Methylevoxine, and Perfamine 83
3-Prenylquinoline Alkaloids 84
2 Acridone Alkaloids 89
Chapter 8 P-Phenethylamines and the lsoquinoline Alkaloids 92
By N. J. McCorkindale
1 General 92
2 PPhenethylamine Alkaloids 93
3 Simple Isoquinoline Alkaloids 102
4 NaphthalenoisoquiadineA lkaloids 106
5 BenzylisoquinolineA lkaloids 108
6 Pavine Alkaloids 112
7 Dibenzopyrrocoline Alkaloids 113
8 Morphine Alkaloids 115
9 Colchidne Alkaloids 124
10 Cularine Alkaloids 126
11 Protoberberine Alkaloids 127
12 Protopine Alkaloids 138
13 Benzophenanthridine Alkaloids 139
14 PhthalideisoquinolineA lkaloids 142
15 Rhoeadtne and Papavermbine Alkaloids 144
16 Spirobenzylisoquinoline Alkaloids 145
17 Ipecacuanha Alkaloids 147
18 Dimeric Benzylisoquinoline Alkaloids 148
...
The Alkaloids
Vlll
Chapter 9 The Aporphinoids 152
By M. Shamma
1 Introduction 152
2 Proaporphines 152
3 Aporphines 154
4 Oxoaporphines 162
5 Aporphine-Benzylisoquinoline Dimers 165
6 Phenanthrenes 165
7 Dioxoaporphines, Aristolactams, and Aristolochic Acid 165
8 Azafluoranthenes 166
9 1,6-Diazafluoranthenes 166
Chapter 10 Amaryllidaceae and Related Alkaloids 167
By K A. Snieckus
Chapter 11 Erythrina and Related Alkaloids 176
By K A. Snieckus
Chapter 12 lndole Alkaloids 183
By J. E. Saxton
1 Introduction 183
2 Simple Alkaloids 184
Non-tryptamines 184
Non-isoprenoid Tryptamines 184
3 Imprenoid Tryptamine and Tryptophan Alkaloids 191
Mould Metabolites 191
Ergot Alkaloids 194
Monoterpenoid Alkaloids 198
Alkaloids of Aristotele Species 198
Corynantheine-Heteroyohimbine-Yohirnbine Group,
and Related Oxindoles 198
Sarpagine-Ajmaline-Picraline Group 215
Strychnine-Akuammicine-Condylocarpine-
Ellipticine-Uleine Group 220
Aspidospermine-Aspidofractine-Eburnamine Group 222
Ibogamine-Cleaveamine Group 23 1