M. Miyazawa, S. Okamura, H. Kameoka
May 1, 1999
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3
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Journal
Journal of Chemical Technology & Biotechnology
Abstract
The microbial transformations of 2,6- and 3,5-dimethylcyclohexanone were investigated using the plant pathogenic fungus, Glomerella cingulata. With this organism 2,6- and 3,5-dimethylcyclohexanone gave the corresponding 2,6- and 3,5-dimethylcyclohexanol. The metabolites from 2,6-dimethylcyclohexanone indicated enantioselective reduction by specific optical rotation of the products. The enantiomeric excesses of the microbiological reduction products were determined by 1H-NMR spectra of (+)-MTPA-esters of the alcohols produced. The reduction of 2,6-dimethylcyclohexanone was stereospecific, with the (2R,6R)-ketone being converted to the corresponding (2R,6R)-(−)-2,6-dimethylcyclohexanol; absolute configuration, 70% ee. On the other hand, 3,5-dimethylcyclohexanone gave the (1α,3α,5α)-3,5-dimethylcyclohexanol (74%) and (1α,3β,5β)-3,5-dimethylcyclohexanol (26%). © 1999 Society of Chemical Industry