Preparation of Optically Pure cis-2, 4-Dimethyl-1-cyclohexanones, the Key Intermediates in Cycloheximide Synthesis, Using Microbial Resolution

抄録

Asymmetric hydrolysis of acetate (10) of (±)-t-2, t-4-dimethyl-r-1-cyclohexanol with Bacillus subtilis var. niger gave (-)-(1S, 2S, 4S)-2, 4-dimethyl-1-cyclohexanol (6a) and (+)-(1R, 2R, 4R)-acetate (10b) with high optical purities. Optically pure (-) and (+)-alcohols (6a and 6b) were prepared via corresponding 3, 5-dinitrobenzoates. Oxidation of alcohols (6a and 6b) with chromic acid gave optically pure (-)-(2S, 4S) and (+)-(2R, 4R)-2, 4-dimethyl-1-cyclohexanones (2a and 2b), respectively.