Carotenoids Volume 2: Synthesis
George Britton, Synnl/Jve Liaaen-Jensen and Hanspeter Pfander This book, Volume 2 in the series Carotenoids, is the first book to be published that is devoted entirely to the total synthesis of carotenoids, but it is timely in view of the rapid developmen
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Carotenoids Volume 2: Synthesis Edited by
G. Britton S. Liaaen-Jensen H. Pfander
Birkhauser Verlag Basel· Boston· Berlin
Editors: Dr. George Britton Reader In Blochemistry Department 01 Biochemistry The University 01 Liverpool P.O Box 147 Liverpool L69 3 BX England
Prolessor Dr. Dr. h. c. Synn0ve Liaaen-Jensen Prolessor 01 Organic Chemlstry Organic Chemistry Laboratories Norwegian University 01 Science and Technology The Norwegian Institute 01 Technology N-7034 Trondhelm Norway
Prolessor Dr. Dr. h. c. Hanspeter Plander Institut lür organische Chemie Universität Bern Freiestrasse 3 CH-3012 Bern Switzerland
A CIP catalogue record lor th,s book is available from the Library 01 Congress, Washington D.c.. USA. Deutsche Bibliothek Cataloging-in-Publication Data Carotenoids / ed. by G. Britton. Birkhäuser. NE: Bntton, George IHrsg.1 Vol. 2. Synthesls. - 1996
- Basel; Boston; Berlin:
ISBN-13: 978-3-0348-9325-1 e-ISBN-13: 978-3-0348-9323-7 001: 10,1007/978-3-0348-9323-7
The publisher and editors cannot assume any legal responslbility lor inlormation on the use 01 chemicals, equipment and patents, drug dosage and administration contained in this publication. The respective user must check its accuracy by consultlng other sources of reference in each Individual case. The use of registered names, trademarks, etc. In this publication, even il not identilied as such, does not Imply that they are exempt from the relevant protective laws and regulations or Iree lor general use. This work IS subject to copyright. All rights are reserved, whether the whole or part 01 the material is concerned, specifically the rights 01 translation, repnnting, re-use 01 illustrations, recitation, broadcasting, reproduction on microlilms or in other ways, and storage in data banks. For any kind 01 use the perm iss ion of the copyright holder must be obtained.
© 1996 Birkhäuser Verlag, P.O. Box 133, CH-4010 Basel, SWltzerland Ca me ra-ready copy prepared by D. Kuli and Ch. Bircher, Cover design: Markus Ettench, Basel
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Contents International Advisory Board and List of Contributors ......
. .... XIII
Preface ... Editors' Notes .....
. ... XVII ........................................................................ XIX
Chapter 1: General Aspects Part I: Synthesis in Perspective Hanspeter Pfander, Synn¢ve Liaaen-Jensen and George Britton ..
Part II: Strategies for Building the Carbon Skeleton Milan Soukup, Paul Spurr and Erich Widmer
A. Introduction 7 B. General Strategies.. .... 7 C. Examples . ..... II 1. Wittig reaction: Astaxanthin and zeaxanthin........................... ............ II 2. Julia sulphone coupling: Zeaxanthin 12 3. Wittig reaction with unsymmetrical carotenoids: (S)-Trisanhydrobacterioruberin ...... 12 4. Dimerization: ~,~-Carotene ......... 13
References
..... 14
Part III: Characterization of Products Hans Mayer and Urs Hengartner
A. Introduction B. Isomers of ~,~-carotene .. C. (7Z)-Lycopene ..
.. .................................................. 18
D. Lutein ... ............................
