STEREOCHEMISTRY OF THE MICROBIAL GENERATION OF DELTA-DECANOLIDE, GAMMA-DODECANOLIDE, AND GAMMA-NONANOLIDE FROM C18 13-HYDROXY, C18 10-HYDROXY, AND C19 14-HYDROXY UNSATURATED FATTY-ACIDS

(S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.