Several studies were completed in which optically active hydroaromatic alcohols were prepared by microbial reduction and their configurations elucidated. One alcohol (+)-trans-1-hydroxy-2-bromoindane, 1, was prepared by microbial reduction (Cryptococcus macerans) of 2-bromoindan-1-one and its absolute stereochemistry was established as 1S,2S by conversion to (-)-1R-indanol. Stereospecific chemical transformations of the acetate of 1 were then employed to prepare (-)-cis- and (-)-trans-1, 2-indane diol. This information has been used to assign the configuration of metabolites (rabbit) of indene and 2-indanone. Microbial reductions of three isomeric acylpyridines were also carried out to clarify the configurations assigned to the alcohols. In each case reduction yielded the S alcohol in high chemical and optical yield. Their configurations were established by transformation to methyl-(S)-O-acetyllactate. These studies, in conjunction with earlier work, demonstrate the stereospecific nature of these reductions and their value to determining the structure of metabolites and natural products.
NIH ExPorter
NIH ExPorter