Issue 3, 1991

An alternative approach to mevinic acid analogues from methyl (3R)-(–)-3-hydroxyhex-5-enoate and an extension to unambiguous syntheses of (6R)-(+)-and (6S)-(–)-goniothalamin

Abstract

Ozonolysis of the 3-silyloxyhexenoate 12, derived from the yeast reduction product methyl (3R)-(–)-3-hydroxyhex-5-enoate 6 and having an enantiomeric enrichment of 78%, followed by Wittig homologation and selenolactonization leads to the unsaturated mevinic acid analogues 17 and 18. Subsequent dehydration gives both enantiomers of the natural product goniothalamin 20 and 21.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 519-523

An alternative approach to mevinic acid analogues from methyl (3R)-(–)-3-hydroxyhex-5-enoate and an extension to unambiguous syntheses of (6R)-(+)-and (6S)-(–)-goniothalamin

F. Bennett, D. W. Knight and G. Fenton, J. Chem. Soc., Perkin Trans. 1, 1991, 519 DOI: 10.1039/P19910000519

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