The Alkaloids Vol.13

347 Pages·1983·21.21 MB·English

by  Royal Society of Chemistry (Great Britain)

The Alkaloids
Volume 13

A Specialist Periodical Report
The Alkaloids
Volume 13
A Review of the Literature Published
between July 1981 and June 1982
Senior Reporter
M. F. Grundon School of Physical Sciences, New University of
Ulster, Coleraine, North Ireland
Reporters
W. A. Ayer University of Alberta, Canada
K. W. Bentley University of Technology , Loughborough
A. S. Chawla Panjab University, Chandigarh, India
R. Dharanipragada University of West Virginia, U.S.A.
G. Fodor University of West Virginia, USA.
H. Guinaudeau University of Limoges, France
D. M. Harrison New University of Ulster
R. B. Herbert University ofL eeds
A. H. Jackson University College, Cardiff
J. A. Lamberton C.S.I.R.O., Melbourne, Australia
J. R. Lewis University ofA berdeen
S. W.P age University of Georgia, U.S.A.
S. W.P elletier 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
ISBN 0-85186-367-1
ISSN 0305-9707
Copyright @ 1983
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 offset by
J. W. Arrowsmith Ltd., Bristol, England
Made in Great Britain
Foreword
Once again an annual review of the alkaloid literature is provided
and this time there is a two-year coverage of Lycopodium Alkaloids.
In an effort to cope with rising costs of production this Volume
has been produced from camera-ready copy and I am grateful to the
authors for their willing co-operation.
It is now apparent, however, that the Specialist Periodical
Reports on "The Alkaloids", "Biosynthesis" , "Terpenoids and Steroids"
and "Aliphatic and Related Natural Product Chemistry" are not
financially viable in their present book format and in 1984 they are
to be replaced by a review journal to be called "Natural Product
Reports". The new journal is to be published every two months and
will continue to give comprehensive annual surveys of the four areas
of natural product research: additional articles on subjects not
covered by existing Specialist Periodical Reports on topics such as
chemotaxonony and enzymology and on advances in physical techniques
will be included periodically and author and subject indices are to
be provided. The flexible production timetable should ensure more
rapid publication of manuscripts compared with S.P.B.'s. In order
to maintain continuity the S.P.R. Senior Reporters are men-hers of
the Editorial Board of Natural Products Reports and in the case of
the alkaloid chapters it is expected that the present authors will
contribute to the Journal. We all hope that the support we have
received over the years from alkaloid chemists will be extended to
this new and exciting venture. As always comments and suggestions
will be much appreciated.
May 1983 M. F. GRUNWN

Cont en
ts
Chapter 1 Biosynthesis 1
By R.B.Herbert
1 Pyrrolidine and Piperidine Alkaloids 1
1.1 Nicotine 1
1.2 Cocaine and Cuscohygrine 3
1.3 6-Pyrazol-1-ylalanine 3
1.4 Pyrrolizidine Alkaloids 4
1.5 Anabasine 4
1.6 The Early Stages of Alkaloid Biosynthesis 5
2 Phenethylamine and Isoquinoline Alkaloids 7
2.1 Norlaudanosoline Synthase 8
2.2 Hordenine and Normacromerine 9
2.3 Hasubanonine, Protostephanine, and Laurifinine 9
2.4 Aporphine Alkaloids 10
2.5 Bisbenzylisoquinoline Alkaloids 11
2.6 Aristolochic Acid 12
3 Alkaloids Derived from Tryptophan 13
3.1 f3-Carboline Alkaloids 13
3.2 Terpenoid Indole Alkaloids 14
3.3 Ergot Alkaloids 15
3.4 Cyclopiazonic Acid 18
3.5 Streptonigrin 18
3.6 Penitrem 20
3.7 Roquefortine 20
3.8 Hinnuliquinone 21
4 Miscellaneous 22
4.1 Geldanomycin, Rifamycin, and Antibiotic A23187 22
4.2 Phenazines and Phenoxazinones 25
4.3 Pseurotin A 29
4.4 Cytochalasins 30
4.5 Cycloheximide 31
4.6 Streptothricin 31
4.7 B-Lactam Antibiotics 33
4.8 Acridone Alkaloids 37
viii The Alkaloids
4.9 Malonomicin 37
References 39
Chapter 2 Pyrrolidine, Piperidine, and Pyridine
Alkaloids 44
By A.R. Pinder
1 Pyrrolidine Alkaloids 44
1.1 Sceletiurn Alkaloids 46
2 Piperidine Alkaloids 46
2.1 Decahydroquinoline Alkaloids 49
2.2 Spiropiperidine Alkaloids 50
3 Pyridine Alkaloids 50
References 53
Chapter 3 Tropane Alkaloids 55
By G. Fodor and R. Dharanipragada
1 Occurrence and Structure of New Alkaloids 55
2 Synthesis and Chemical Transformations 57
3 Pharmacology 62
4 Analytical Studies 63
References 63
Chapter 4 Pyrrolizidine Alkaloids 65
By D.J. Robins
1 Synthesis of Macrocyclic Pyrrolizidine Alkaloids 65
2 Synthesis of Necine Bases 69
3 Alkaloids of the Boraginaceae 72
4 Alkaloids of the Compositae 73
5 Alkaloids of the Leguminosae 74
6 Alkaloids in Micro-organisms 75
7 Alkaloids in Insects 75
8 General Studies 76
9 Pharmacological and Biological Studies 77
References 79
Chapter 5 Indolizidine Alkaloids 82
By J. A. Lamberton
1 Swainsonine 82
2 Prosopis Alkaloids 82
3 Elaeocarpus Alkaloids 83
4 Dendrohates Alkaloids 84
5 Other Syntheses 85
References 86