Abstract
The mode of transformation in Beauveria bassiana (ATCC 7159) of ketones 5–9 and 16 has been studied and compared with that of C-6--C-4 2, which through raspberry ketone 1 gives rise to C-6--C-2 tyrosol 3. Of the fed materials, only product 5 behaves as 2, i.e., is a good substrate for a formal Baeyer-Villiger chain-shortening transformation, which provides the secondary carbinol 10 enriched in the ( S) enantiomer. Stereochemical analysis of the products obtained in the incubation of an authentic sample of ( S) 5, obtained with baker's yeast upon reduction of the corresponding unsaturated ketone, indicates that the Baeyer-Villiger degradation leading to 10 occurs with kinetic preference for the ( S) enantiomer and retention of configuration at the migrating carbon atom.
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