Biological stereoselective reduction of 2,6- and 3,5-dimethylcyclohexanones by Glomerella cingulata

✍ Scribed by Mitsuo Miyazawa; Shigeaki Okamura; Hiromu Kameoka

• Book ID: 101264727
• Publisher: Wiley (John Wiley & Sons)
• Year: 1999
• Tongue: English
• Weight: 80 KB
• Volume: 74
• Category: Article
• ISSN: 0268-2575
• DOI: 10.1002/(sici)1097-4660(199905)74:5<399::aid-jctb50>3.0.co;2-2

✦ Synopsis

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 3,5dimethylcyclohexanone gave the corresponding 2,6-and 3,5-dimethylcyclohexanol. The metabolites from 2,6-dimethylcyclohexanone indicated enantioselective reduction by speci®c optical rotation of the products. The enantiomeric excesses of the microbiological reduction products were determined by 1 H-NMR spectra of ()-MTPA-esters of the alcohols produced. The reduction of 2,6-dimethylcyclohexanone was stereospeci®c, with the (2R,6R)-ketone being converted to the corresponding (2R,6R)-(À)-2,6-dimethylcyclohexanol; absolute con®guration, 70% ee. On the other hand, 3,5dimethylcyclohexanone gave the (1a,3a,5a)-3,5-dimethylcyclohexanol (74%) and (1a,3b,5b)-3,5dimethylcyclohexanol (26%).