On the stereochemistry of the Baeyer-Villiger degradation of arylalkyl-ketone structurally related to raspberry ketone by Beauveria bassiana

Article abstract of DOI:10.1016/0957-4166(96)00413-2

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. Copyright (C) Elsevier Science Ltd.