Stereoselective reduction of 2-substituted cyclohexanones by Saccharo-mycescerevisiae.

A comparative study of two modifications of enzymic reduction of ethyl N-\2-\4-[(2-oxo-cyclohexyl)methyl]phe- noxy\ethyl\ carbamate (1), an insect juvenile hormone bioanalog, was performed using Saccharomyces cerevisiae in two bioreactors of different size, 250-ml shake-flask and 1-l fermenter. The two major products of this reduction were obtained in 45–49% (w/w) yields but with > 99% enantiomeric purity. Their absolute configurations were assigned as ethyl (1S,2S)-N-\2-\4-[(2-hydroxycyclohexyl)methyl]phenoxy\ethyl\carbamate (2a) and ethyl (1R,2S)-N-\2-\4-[(2-hydroxycyclohexyl)methyl]phenoxy\ethyl\carbamate (3a). [ABSTRACT FROM AUTHOR]