65942-08-7Relevant articles and documents
Enzymes in Organic Synthesis. 34. Preparations of Enantiomerically Pure Exo-and Endo-Bridged Bicyclic and Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Meso Diols
Lok, Kar P.,Jakovac, Ignac J.,Jones, J.Bryan
, p. 2521 - 2526 (2007/10/02)
Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidations of saturated and unsaturated exo- and endo-bridged bicyclic and meso diols proceed with complete enantiotopic specificity to give high (64-87percent) yields of the corresponding chiral lactones of >=97percent ee.As for previous meso diol oxidations, the stereochemical course of each oxidation (S-center CH2OH oxidation in all cases) is as predicted by the cubic-space model of the active site.An illustration of the asymmetric synthetic value of these chiral lactones is provided by the conversion of one of them into a prostaglandin precursor.