Alkaloids: Chemistry and Pharmacology, Volume 12

657 Pages·1970·25.16 MB·English

by  R.H.F Manske

THE ALKALOIDS
Chemistry and Physiology
VOLUME XI1
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THE ALKALOIDS
Chemistry and Physiology
Edited by
R. H. F. MANSKE
UniRoyal Limited Research Laboratory
Cuelph, Ontario, Canada
VOLUME XI1
1970
ACADEMIC PRESS NEW YORK LONDON
COPYRIGHT0 1970, BY ACADEMIPCR ESSI,N C.
ALL RIGHTS RESERVED,
NO PART OF THIS BOOK MAY BE REPRODUCED IN ANY FORM,
BY PHOTOSTAT, MICROFILM, RETRIEVAL SYSTEM, OR ANY
OTHER MEANS, WITHOUT WRITTEN PERMISSION FROM
THE PUBLISHERS.
ACADEMIC PRESS, INC.
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United Kingdom Edition published by
ACADEMIC PRESS, INC. (LONDON) LTD.
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LIBRARYO F CONGRESSC ATALOGC ARDN UMBER50: -5522
PRINTED IN THE UNITED STATES OF AMERICA
LIST OF CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors’ contributions begin.
E. G. C. CLARKET, he Royal Veterinary College, University of London,
London, England (513)
L. H. KEITH, Department of Chemistry, The University of Georgia,
Athens, Georgia (xv, 1, 135)
R. H. F. MANSKEU, niRoyal Limited Research Laboratory, Guelph,
Ontario and the University of Waterloo, Waterloo, Ontario, Canada
(455)
S. W. PELLETIEDRep, artment of Chemistry, The University of Georgia,
Athens, Georgia (xv, 1, 135)
F. ~ANTAV+’, Institute of Chemistry, Medical Faculty, Palack$
University, Olomouc, Czechoslovakia (333)
J. E. SAXTONT,h e University, Leeds, England (207)
FRANK L. WARREN, C.S.I.R. Natural Products Research Unit,
University of Cape Town, Rondebosch, Cape Province, South Africa
(245)
V
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PREFACE
The proliferation of alkaloid literature which has been so marked for
several decades has continued. The discovery of new sources of known
alkaloids and the discovery of new alkaloids in new and already
examined sources together with new structural and synthetic studies
call for periodic reviews. This volume is an attempt to bring some of
the alkaloid chemistry up-to-date. As in the more recent volumes we
have chosen a number of subjects which seem appropriate at this time.
Entries in the Subject Index are restricted to topics which are basic
to the substances or groups under discussion; incidental mention does
not necessarily merit inclusion. The abbreviations used for journals in
literature references are those found in Chemical Abstracts List of
Periodicals.
Once more the editor, on behalf of the publisher and himself, takes
this opportunity to express his indebtedness to the conscientious and
competent authors who have made the publication of this volume
possible.
R. H. F. MANSKE
Guelph, Ontario
December, 1969
vii
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CONTENTS
LIST OF CONTRIBUTO.R.S.. ............................................... V
PREFACE.. ............................................................. vii
CONTENTSOFPREVIOUSVOL.U..M..E.S. ................................... xi
The Diterpene Alkaloids: General Introduction
S . W . PELLETIEANRD L . H . KEITH
Text ......................................................... xv
Chapter 1. Diterperie Alkaloids from Aconitum. Delphinium. and
Garryn Species: The (219-Diterpene Alkaloids
S . W . PELLETIEARN D L . H . KEITH
I . Introduction .................................................... 2
I1. Lycoctonine-Type Alkaloids ....................................... 10
I11 . Aconitine-Type Alkaloids ......................................... 40
IV. Lactone-Type Diterpene Alkaloids ................................. 109
V. Uncharacterized Alkaloids ........................................ 118
References ...................................................... 129
Chapter 2 . Diterpene Alkaloids from Aconitum. Delphinium. and
Garrya Species: The (220-DiterpeneA lkaloids
S . W . PELLETIEANRD L . H . KEITH
I . Introduction .................................................... 136
I1 . The Garrya Alkaloids ............................................. 136
I11 . The Atisine Alkaloids ............................................. 143
IV. Correlations and Absolute Stereochemistry of Atisine and Garrya Alkaloids 155
V. The Ternary Iminium Salts of the Atisine and Gtarrya Alkaloids ......... 166
VI . The Chemistry of Alkaloids with a Modified Atisine Skeleton ........... 174
VII. Synthesis of Diterpene Alkaloids ................................... 188
References ...................................................... 202
Chapter 3 . Alkaloids of Alstoriin Species
J . E . SAXTON
I . Occurrence ...................................................... 207
I1 . Venenatine. Isovenenatine. and Venoxidine .......................... 209
I11 . Tetrahydroalstonine. Alstoniline. and Echitamine .................... 211
IV . Villalstonine .................................................... 213
V . Alstophylline .................................................... 223
ix