Yeast-mediated synthesis of optically active diols with C 2-symmetry and ( R)-4-pentanolide

Abstract

Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give ( R)-alcohols. (2 R,5 R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2 R,4 R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and ( R)-4-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.