Asymmetric Reduction by Yeasts. Formation of Optically Active Synthons having two Chiral Centers Useful for Natural Product Synthesis

Abstract

Asymmetric reduction of α-methyl β-keto ester and β-methyl α-keto ester by means of yeasts was carried out. Both keto esters were found to be reduced by a variety of yeasts to give optically active hydroxy esters having two chiral centers. The absolute configuration and the optical purity of the reduction products were primarily determined by measuring the 400 MHz NMR spectra of the (+)-MTPA esters of the alcohols produced. The successful use of the chiral synthons prepared by the present method in high optical purity to the synthesis of (-)-oudemansin is described. © 1983, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.