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Synthesis of Bicyclic Homochiral Dienes by Allylic Rearrangement of Cyclohexenols – Suitable Building Blocks for The Synthesis of Nagilactones

✍ Scribed by Westermann, Bernhard ;Dubberke, Silke

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
649 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

A very short and straightforward synthesis towards highly functionalized dienes is described. The homochiral starting material, unsaturated β‐oxo ester 2, can be prepared by enzyme‐catalyzed saponification. The utility of the dienes has been demonstrated in a cycloaddition with N‐phenyltriazolidinone as the dienophile. The Diels‐Alder reaction is highly diastereoselective, yielding only one diastereomer.

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