TY - JOUR
T1 - Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide
AU - Ikeda, Hajime
AU - Sato, Eriko
AU - Sugai, Takeshi
AU - Ohta, Hiromichi
PY - 1996/6/10
Y1 - 1996/6/10
N2 - 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. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-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.
AB - 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. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-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.
UR - http://www.scopus.com/inward/record.url?scp=0030006659&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030006659&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(96)00373-0
DO - 10.1016/0040-4020(96)00373-0
M3 - Article
AN - SCOPUS:0030006659
SN - 0040-4020
VL - 52
SP - 8113
EP - 8122
JO - Tetrahedron
JF - Tetrahedron
IS - 24
ER -