Table Of ContentA Specialist Periodical Report
The Alkaloids
Volume 2
A Review of the Literature Published
between July 1970 and June I971
Senior Reporter
J. E. Saxton, Department of Organic Chemistry,
The University of Leeds
Reporters
H. 0. Bernhard, University of Waterloo, Canada
R. Goutarel, Centre Nationale de la Recherche
Scientifique, Gif -sur- Yvette, France
J. A. Joule, Manchester University
Mme. F. Khuong-Huu, Centre Nationale de la Recherche
Scientifique, Gif-sur- Yvette, France
. S. W. Pelletier, University of Georgia, U.S.A.
V. A. Snieckus, University of Waterloo, Canada
J. Staunton, Cambridge University
L. H. Wright, University of Georgia, U.S.A.
ISBN:0 85186 267 5
0 Copyright 1972
The Chemical Society
Burlington House, London, W1 V OBN
Foreword
The first volume in this series was, perhaps, mi generis, in that it comprised
reviews of developments in alkaloid chemistry over an eighteen-month period
instead of the twelve-month period adopted for subsequent Reports. There was
also included sufficient background material to enable the new work to be
placed in perspective in its own particular area, as well as three summaries of a
more extended kind; these were concerned with the biosynthesis of the terpenoid
indole alkaloids, the bisindole alkaloids, and alkaloids of current pharmacological
or clinical interest.
This second volume, which reviews the alkaloid literature from July 1970
to June 1971, approaches more closely the standard Specialist Periodical Report
originally envisaged by the Chemical Society and adopts a form which, with
minor variations, will very probably be followed in subsequent volumes. Once
again the whole field of alkaloid chemistry has been reviewed, with the exception
of the Steroidal Alkaloids of the Solanum and Veratrum Groups. The omission
of these groups in the first volume was deliberate; their inclusion in the second
volume was intended, but proved to be impracticable, and we hope to remedy
this omission in the third volume, It is fortunate, however, that this particular
area can quite properly be discussed in a volume devoted to alkaloids or in one
devoted to steroids; and for a brief review of recent developments in this subject
the reader is meanwhile referred to the SpecialistP eriodical Report on Terpenoids
and Steroids, Volume One (Senior Reporter Dr. K. H. Overton).
Once again it is a pleasure to acknowledge the ready co-operation of my
colleagues in the preparation of this Report, and my indebtedness to them for
the efforts they made to ensure the punctual submission of their manuscripts.
Suggestions concerning the presentation of subsequent Reports in this series
will, as always, be welcomed.
J. E. Saxton
Set in Times on Monophoto Filmsetter and printed offset by
J. W. Arrowsmith Ltd., Bristol, England
Made in Great Britain
Contents
Chapter 1 Biosynthesis
By J. Staunton
Terpenoid Indole Alkaloids 1
Eburnamine-Vincamine Alkaloids 3
Cinchona Alkaloids 4
Ipecac Alkaloids 6
Ergot Alkaloids 8
Miscellaneous Indole Alkaloids 9
Isoquinoline Alkaloids 10
Amaryllidaceae Alkaloids 16
Lysine and the Piperidine Alkaloids 20
Coniine 26
H yosc yamine 27
Ty lophorine 27
Quinoline Alkaloids 28
Arborine 29
Annuloline 31
Dolichotheline 32
Chapter 2 Pyrrolidine, Piperidine, and Pyridine Alkaloids
By V. A. Snieckus
1 Pyrrolidine Alkaloids 33
2 Piperidine Alkaloids 35
Alkaloids
3 Pyridine Alkaloids 43
4 Mono- and Sesqui-terpenoid Alkaloids 45
Chapter 3 Tropane Alkaloids 54
By J. E. Saxton
Chapter 4 The Pyrrolizidine Alkaloids
By J. E. Saxton
1 The Necine Bases and Simple Related Alkaloids 59
2 The Ester Alkaloids 60
3 Pharmacological Aspects 65
Chapter 5 The lndolizidine Group
By J. E. Saxton
1 Zpomoea Alkaloids 69
2 Slaframine 71
3 Elaeocarpus Alkaloids 72
4 The Tylophorine Group 74
Chapter 6 The Quinolizidine Alkaloids
By J. E. Saxton
1 LupineGroup 79
2 Ormosia Alkaloids 84
Chapter 7 Quinoline, Quinazoline, Acridone, and
Related Alkaloids
By V. A. Snieckus
1 Quinoline Alkaloids 86
2 Quinazoline Alkaloids 91
3 Acridone Alkaloids 95
Contents vii
Chapter 8 p- Phenethylamines and the lsoquinoline
Alkaloids
By H. 0. Bernhard and V. A. Snieckus
1 g-Phenethylamines 97
2 Simple Isoquinoline Alkaloids 99
3 Benzylisoquinoline Alkaloids 106
A. Simple Benzylisoquinolines 107
B. Pavine Alkaloids 114
C. Proaporphine, Aporphine, and Homoproaporphine
Alkaloids 114
D. Morphine Alkaloids 128
Homomorphinandienone (Androcymbine) Alkaloids 143
E. Colchicine Alkaloids 144
F. Cularine 145
G. Protoberberine Alkaloids 147
H. Protopine Alkaloids 156
I. Phthalideisoquinoline and Rhoeadine Alkaloids 158
J. Benzophenanthridine Alkaloids 161
K. Spirobenzylisoquinoline Alkaloids 166
L. Ipecacuanha Alkaloids 169
4 Dimeric Benzylisoquinoline Alkaloids 170
Chapter 9 Amaryllidaceae and Related Alkaloids 185
By V. A. Snieckus
Chapter 10 Erythrina and Related Alkaloids 199
By V. A. Snieckus
Chapter 11 lndole Alkaloids
By J. A. Joule
1 Simple Alkaloids 209
Non-tryptamines 209
Non-isoprenoid Tryptamines 21 1
2 Isoprenoid-tryptaminea nd -tryptophan Alkaloids 212
Non-terpenoid Alkaloids 212
Monoterpenoid Alkaloids 213
Yohimbine-Corynantheine (and Related Oxindoles)
Group 213
...
Alkaloids
Vlll
Sarpagine-Ajmaline-Picraline Group 217
Strychnine-Akuammicine/Cond y locarpine--Uleine
Group 220
Eburnamine-Aspidospermine-Aspid ofractin ine
Group 226
Ibogaine-Cleavamine Group 23 1
Skeletal Rearrangements and Int erconversi on s 23 1
3 Biogenetically Related Quhohe Alkaloids 235
4 Bisindole Alkaloids 238
Chapter 12 Lycopodium Alkaloids 242
By V. A. Snieckus
Chapter 1 3 Recent Developments in Diterpenoid Alkaloid
Chemistry
By S. W. Pelletier and L. H. Wright
1 Introduction 247
2 Newstructures 248
Anhydroignavinol 248
H ypognavinol 249
Vakognavine 249
Lap paconidine 25 1
Lappaconitine 25 1
Talatizamine and Cammaconine 252
Absolute Configuration of Condelphine and its Relatives 253
A Revision of Structure for Certain Delphinine and
Aconitine Alkaloids 254
3 Chemistry and Synthesis 256
Lappaconine Rearrangements 256
Diacetyltalatizamine Pyrolysis 257
Synthesis of an Atisine-type Intermediate 257
Synthesis of a Veatchine-type Intermediate 258
Chapter 14 Steroidal Alkaloids of the Apocynaceae and
Buxaceae
By F. Khuong-H uu and R. Goutarel
Introduction 259
