Yeast-mediated synthesis of optically active diols with C2-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.