The Alkaloids: Chemistry and Pharmacology 26 PDF
Preview The Alkaloids: Chemistry and Pharmacology 26
THE ALKALOIDS Chemistry and Pharmacology Volume 26 This Page Intentionally Left Blank THE ALKALOIDS Chemistry and Pharmacology Edited by Arnold Brossi National Institutes of Health Bethesda, Maryland VOLUME 26 1985 ACADEMIC PRESS, INC. Harcourt Brace Jovanovich, Publishers Orlando San Diego New York Austin London Montreal Sydney Tokyo Toronto COPYRIGHT o 1985 BY ACADEMIC PRESS,I NC. ALL RIGHTS RESERVED. NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WFUTING FROM THE PUBLISHER. ACADEMIC PRESS, INC. Orlando, Florida 32887 United Kingdom Edition published by ACADEMIC PRESS INC. (LONDON) LTD. 24-28 Oval Road, London NWI 7DX LIBRARYO F CONGRESS CATALOG CARD NUMBER: 50-5522 ISBN: 0-12-469526-4 PRINTED IN THE UNITED STATES OF AMERICA 85 86 87 88 987654321 CONTENTS CONTRIBUTOR..S. ........................................................ ix PREFACE. ............................................................... xi Chapter . Simple Indole Alkaloids Including p-Carbolines and Carbazoles HENRI-PHILIPPHEU SSON I. Introduction .......................................................... 1 11. Occurrence . .......................................................... 2 111. Nontryptamine Alkaloids ................................................ 2 IV. Nonisoprenoid Tryptamine Alkaloids ...................................... 26 ... ........ 41 ................................... 45 ............................... 46 Chapter 2. Sulfur-Containing Alkaloids JERZYT . WR6BEL I. Introduction ..................................... 54 11. Alkaloids wi Side Chain ............ 111. Alkaloids with One Sulfur Atom in the Ring IV. Alkaloids with More than One Sulfur Atom V. Sulfur-Containing Alkaloids of Peptide StNC References . . ......... Chapter 3. Pyridine and Pipendine Alkaloids GEORGEM . STRUNZA ND JOHNA . FINDLAY I. Introduction ........................................................... 89 11. 2,6-Disubstituted Pipendin-3-01s .......................................... 90 111. Other Piperidin-3-01s ................................................... 102 V vi CONTENTS IV . Pinus Alkaloids ........................................................ 105 V . Other 2,6 -Disubstituted Piperidines ....................................... 108 VI . Sedum Alkaloids ...................................................... 113 VII . Tobacco Alkaloids, Related Compounds, and Other Nicotinic Acid Derivatives ... 121 VIII . Piperidine Metacyclophane Alkaloids ....................... .... 152 IX . Pipecolic Acid Derivatives ............................................... 153 X . Terpenoid Alkaloids .................................................... 154 XI . Miscellaneous Pyridine Alkaloids ......................................... 159 References ............................................................ 174 Chapter 4. Benzophenanthridine Alkaloids v . SlMhNEK I . Introduction ........................................................... 185 I1 . Occurrence of Benzophenanthridine Alkaloids ............ 111 . Isolation and Analytical Methods .......... IV . Stereochemistry and Spectral Characteristics . V . Chemical Reactivity and Conversions of Benzo ......... 204 VI . Synthesis ............................................................. 209 VII . Biosynthesis ...... .. .... 225 VIII . Biological Activity ..................................................... 229 Addendum ........................................................... 230 References . . ..................................... 234 Chapter 5 . Lycopodium Alkaloids D . B . MACLEAN .................................................... 241 I1 . The Alkaloids and Their Occurrence ....................................... 242 I11 . Synthesis of the Alkaloids ........................................... 269 IV . Biosynthesis and Biogenesis ............................................. 290 V . Chemotaxonomy ....................................................... 294 References ........................ ....................... 296 Chapter 6 . Peptide Alkaloids ULRICHS CHMIDTA. LBRECHLTI EBERKNECHATN.D ERNSTH ASLINGER I . Introduction ........................................................... 299 I1 . Structural and Conformational Studies ..................................... 301 .I11. New Peptide Alkaloids Isolated and Elucidated .............................. 304 IV . Synthesis of Peptide Alkaloids ........................................... 311 References ........................................................... 325 CONTENTS vii Chapter 7 . Pyrrolizidine Alkaloids JERZYT . WR6BEL I . Introduction ........... ................................... 327 I1 . Pyrrolizidine Alkaloids: St inations. New Compounds ............ 327 111 . Syntheses of Pyrrolizidine Alkaloids ....................................... 339 IV . Syntheses of Necine Bases .................................... 346 V . Biosynthesis ................................... ........... 370 VI . Spectroscopy ................................................... 379 VII . Toxicity and Pharmacology ... ........................... 381 References ............................................... 382 CUMULATIVINE DEXO F TITLES ............................................. 385 CUMULATIVINE DEXO F CONTRIBUTO.R.S. .................................... 391 SUBJECTIN DEX. ......................................................... 393 This Page Intentionally Left Blank Numbers in parentheses indicate the pages on which the authors’ contributions begin. JOHN A. FINDLAY(8 9), Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, Canada E3B 6E2 ERNSTH ASLINCE(R29 9), Institute for Organic Chemistry, University of Vienna, A 1090 Vienna, Austria HENRI-PHILIPPHEU SSON( l),I nstitut de Chimie des Substances Naturelles, Cen- tre National de la Recherche Scientifique, 91 190 Gif-sur-Yvette, France ALBRECHLTI EBERKNECH(2T9 9), Institute for Organic Chemistry, Biochemistry and Isotope Research, University of Stuttgart, 7000 Stuttgart 80, West Germany D. B. MACLEAN(2 41), Department of Chemistry, McMaster University, Hamil- ton, Ontario, Canada L8S 4M1 ULRICHS CHMIDT(2 99), Institute for Organic Chemistry, Biochemistry and Iso- tope Research, University of Stuttgart, 7000 Stuttgart 80, West Germany V. SIMANEK(1 85), Institute of Chemistry, Palack9 University,775 15 Olomouc, Czechoslavakia GEORGEM . STRUNZ(8 9), Maritimes Forest Research Centre, Canadian Forestry Service, Fredericton, New Brunswick, Canada E3B 5P7 JERZYT . WR~BE(L53 , 327), Department of Chemistry, University of Warsaw, Warsaw 02-093, Poland ix
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