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.