Journal of Organic Chemistry p. 5237 - 5239 (1991)
Update date:2022-09-26
Topics:
Cardillo, Rosanna
Fronza, Giovanni
Fuganti, Claudio
Grasselli, Piero
Mele, Andrea
et al.
(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.
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