A new and efficient chemoenzymatic route to both enantiomers of α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones

Graphic A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones starting from α-methyl-β-methoxy cyclic enones is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis o...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 15; no. 5; pp. 777 - 781
Main Authors Demir, Ayhan S., Fındık, Hamide, Köse, Elif
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.03.2004
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
OXIDATION
MANGANESE(III) ACETATE
ACYLOXY
4-SUBSTITUTED 5-HYDROXY-3-OXOCYCLOPENTENES
PROSTAGLANDIN
COMBINATION
INHIBITOR
FACILE
DERIVATIVES
GRIGNARD
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Summary:Graphic A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones starting from α-methyl-β-methoxy cyclic enones is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of α ′-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of γ-hydroxy-α-methyl cyclic enones 3 and 4 in a high enantiomeric excess.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.12.006