Journal of the American Chemical Society p. 2521 - 2526 (1985)
Update date:2022-08-04
Topics:
Lok, Kar P.
Jakovac, Ignac J.
Jones, J.Bryan
Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidations of saturated and unsaturated exo- and endo-bridged bicyclic <2.2.1> and <2.2.2> 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.
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Doi:10.1002/hlca.19620450710
(1962)Doi:10.1055/s-2007-984907
(2007)Doi:10.1016/S0040-4039(01)81475-1
(1984)Doi:10.1002/recl.19921111102
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(1985)Doi:10.1021/jacs.7b01441
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