ENZYMES IN ORGANIC SYNTHESIS-29. PREPARATIONS OF ENANTIOMERICALLY PURE cis-2,3- AND 2,4-DIMETHYL LACTONES VIA HORSE LIVER ALCOHOL DEHYDROGENASE-CATALYZED OXIDATIONS

Article abstract of DOI:10.1016/S0040-4020(01)82410-8

Further examples of the broad applicability of horse liver alcohol dehydrogenase-catalyzed oxidations of meso-diols as a route to chiral lactones of asymmetric synthetic value are described.The acyclic meso substrates, cis-2,3-dimethyl- and -diethylbutane-1,4-diols, and cis-2,4-dimethylpentane-1,5-diol, are stereospecifically oxidized in good yields to the corresponding enantiomerically pure γ- and δ-lactones.The oxidation of cis-3,4-bis(hydroxymethyl)thiacyclopentane is similarly stereospecific.For each meso-diol the oxidation takes place with a net stereospecifity for the hydroxymethyl groups attached to the S-centers, with the initially formed hydroxyaldehydes undergoing further enzyme-catalyzed oxidations via their hemiacetal forms to produce lactone products directly.