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Enantioselective formal synthesis of tridemethylisovelleral

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Author

Summary, in English

A simple and efficient synthetic route to the bicyclic alpha,beta-unsaturated beta-keto ester methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7ahexahydro-1H-indene-5-carboxylate, a versatile intermediate in the synthesis of biologically active unsaturated 1,4-dialdehydes, is described. The synthesis includes a chirality introducing nonenzymatic asymmetric desymmetrization (ADS) reaction of a cyclic nieso-anhydride 4 and a modified Hofmann method for preparing exocyclic dienes. The ester was synthesized in a moderate overall yield (19%) from 6 and with an excellent enantioselectivity (> 90%).

Publishing year

2007

Language

English

Pages

635-638

Publication/Series

Tetrahedron Letters

Volume

48

Issue

4

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 0040-4039