Progress in the Chemistry of Organic Natural Products

The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics relate

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88 Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products Founded by L. Zechmeister Edited by W. Herz, H. Falk, and G. W. Kirby Authors: J. F. Grove, E. Reimann, S. Roy

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Prof. W. Herz, Department of Chemistry, The Florida State University, Tallahassee, Florida, U.S.A. Prof. H. Falk, Institut fu¨r Chemie, Johannes-Kepler-Universita¨t, Linz, Austria Prof. G. W. Kirby, Chemistry Department, The University of Glasgow, Glasgow, Scotland

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Library of Congress Catalog Card Number AC 39-1015 Typesetting: Thomson Press (India) Ltd., Chennai Printing and binding: Druckerei Theiss GmbH, A-9431 St. Stefan Printed on acid-free and chlorine-free bleached paper SPIN: 10975961 With 12 Figures and 1 coloured Plate

ISSN 0071-7886

ISBN-10 3-211-20688-4 SpringerWienNewYork ISBN-13 978-3-211-20688-1 SpringerWienNewYork

Contents List of Contributors. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . IX

Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds E. Reimann . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

1

1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

2

2. Structural Classification of Erythrina Alkaloids . . . . . . . . . . . . . . . . . . . . . .

4

3. New Erythrina Alkaloids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

18

4. Biosynthesis of Erythrina Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.1. Erythrinane Alkaloids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.2. Homoerythrinane Alkaloids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

18 18 20

5. Syntheses of Erythrina Alkaloids and Erythrina Type Compounds . . . . . . . . 5.1. Methodical Classification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.2. Erythrinanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.2.1. Final Formati