APPLICATION OF MICROBIAL ENANTIOFACIALLY SELECTIVE HYDROLYSIS IN NATURAL PRODUCT SYNTHESIS

Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.