ON THE STEREOCHEMISTRY OF THE BAEYER-VILLIGER DEGRADATION OF ARYLALKYL-KETONES STRUCTURALLY RELATED TO RASPBERRY KETONE BY BEAUVERIA-BASSIANA

The mode of transformation in Beauveria bassiana (ATCC 7159) of ketone s 5-9 and 16 has been studied and compared with that of C-6-C-4 2, whi ch 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 pr ovides the secondary carbinol 10 enriched in the (S) enantiomer. Stere ochemical analysis of the products obtained in the incubation of an au thentic sample of (S) 5, obtained with baker's yeast upon reduction of the corresponding unsaturated ketone, indicates that the Baeyer-Villi ger degradation leading to 10 occurs with kinetic preference for the ( S) enantiomer and retention of configuration at the migrating carbon a tom. Copyright (C) 1996 Elsevier Science Ltd