Enantioselective synthesis of cyclohexenone derivatives by a chemicoenzymatic approach: stereo- and regioselective route to potential intermediates of compactin (ML 236B) and mevinolin.
As a synthetic application of the chiral monoester 2, prepared by pig liver esterase (PLE)-catalyzed hydrolysis of the corresponding meso diester 1, conversion of 2 into various cyclohexenone derivatives was examined. This paper describes the preparation of the isomeric cyclohexenones 6 and 7, potential intermediates for the synthesis of anti-hypercholesmic compactin (ML 236B) and mevinolin, under stereo- and regioselective control.
Kobayashi
S
S
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Eguchi
Y
Y
Shimada
M
M
Ohno
M
M
D055598:Chemical Phenomena; D002621:Chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000302:isolation & purification; D008148:Lovastatin / Q000031:analogs & derivatives* / Q000302:isolation & purification*; D013237:Stereoisomerism
D003512:Cyclohexanones; C012258:mevastatin; D008148:Lovastatin