MICROBIAL STEREO-DIFFERENTIATING REDUCTION OF THE CARBONYL GROUPS LOCATED ON THE C2 AXES OF GYROCHIRAL MOLECULES

The enantiomer selectivity of Curvularia lunata and Rhodotorula rubra with respect to some C2 ketone substrates having the C2 axis coincident with the carbonyl axis was examined. Both microbes exhibited a marked stereodifferentiation between enantiomers of (.+-.)-9-twist-brendanone, (.+-.)-2-brexanone, (.+-.)-D3-trishomocubanone (8), (.+-.)-bisnoradamantanone, (.+-.)-biphenyl, and (.+-.)-.alpha.-binaphthyl bridged ketones, selectively reducing the P-C2 ketone enantiomers.