Studies on the Biosynthesis of Aliphatic Lactones in Sporobolomyces odorus. Conversion of (S)- and (R,S)-13-Hydroxy-(Z,E)-9,11-octadecadienoic Acid into Optically Pure (R)-δ-Decalactone

Article abstract of DOI:10.1021/jo00033a007

The mechanism of the biotransformations of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11-octadecadienoic acid, 1, into optically pure (R)-δ-decalactone, 12, catalyzed by the yeast Sporobolomyces odorus, was studied, and an oxidation of the secondary hydroxy group followed by an enantioselective reduction of the keto acid intermediate was found to be responsible for the stereochemical outcome.