Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C18 13-Hydroxy, C18 10-Hydroxy, and C19 14-Hydroxy Unsaturated Fatty Acids

Article abstract of DOI:10.1021/jo00018a001

(S)-δ-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)-γ-dodecanolide.When (S)-homocoriolic acid (3) was fed to C. suaveolens, γ-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, occured 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 deuterated 10 showed.