Alkaloids: Chemistry and Pharmacology, Volume 12 PDF
Preview Alkaloids: Chemistry and Pharmacology, Volume 12
THE ALKALOIDS Chemistry and Physiology VOLUME XI1 This Page Intentionally Left Blank 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. 111 Fifth Avenue, New York, New York 10003 United Kingdom Edition published by ACADEMIC PRESS, INC. (LONDON) LTD. Berkeley Square House, Loiidon WlX 6BA 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 This Page Intentionally Left Blank 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 This Page Intentionally Left Blank 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
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