Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1986-08-25
1991-09-17
Weimar, Elizabeth C.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435147, 435155, C12P 726, C12P 724, C12P 702, C12P 700
Patent
active
050494970
ABSTRACT:
The enantiomers of formulas ##STR1## are prepared in a sequence starting from the racemic compound of formula ##STR2## wherein X is hydro or bromo when Y is bromo, or X is chloro when Y is chloro. The key step of this process involves a microbial reduction of the compound of formula (3) to give a ketone and an alcohol of high enantiomeric purity.
REFERENCES:
patent: 4130721 (1978-12-01), Bundy et al.
Bucciarelli et al., "Asymmetric Reduction of Trifluoromethyl and Methyl Ketone by Yeast; An Improved Method", Synthesis, vol. 11, 897-899, 1983.
Nakamura et al., "Stereochemical Control in Yeast Reduction", Tet. Lett., vol. 25, 3979-3982, 1984.
Davies et al, "Reduction of 7-Chlorobicyclo[3.2.0]Hept-en-6-one Catalysed by 32, 20.beta.-Hydroxysteroid Dehydrogenase", Tetrahedron Lett. vol. 27, 1093-1094, 1986.
March, Advanced Organic Chemistry, "Oxidations and Reductions", pp. 1048-1120, 1985.
Fersht, "Stereochemistry of Enzymatic Reactions" in Enzyme Structure and Mechanism, pp. 221-247, W. H. Freeman and Company, 1985.
Mori et al., "A New Syntheiss of (+)-6a-Carbaprostaglandin Iz Employing Yeast Reduction of a .beta.-Keto Ester Derived from cis-Bicyclo[3.3.0]Octane-37,-Dione as the Key Step", Tetrahedron, vol. 42, 435-444, 1986.
Newton et al., "Substrate Non-Enantiospecific and Product Enantioselective Reduction of Bicylo9[3.2.0]Hept-2-en-6-one using Yeast" J.C.S. Chem. Comm., pp. 908-909, 1979.
Kertesz Dennis J.
Kluge Arthur F.
Lewis Brian
Lowin David A.
Moran Tom M.
Poulos Gail
Syntex (U.S.A.) Inc.
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