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A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones
Date
2004-03-08
Author
Demir, Ayhan Sıtkı
Findik, H
Kose, E
Metadata
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A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-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 gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess.
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Catalysis
URI
https://hdl.handle.net/11511/57569
Journal
TETRAHEDRON-ASYMMETRY
DOI
https://doi.org/10.1016/j.tetasy.2003.12.006
Collections
Department of Chemistry, Article
Citation Formats
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BibTeX
A. S. Demir, H. Findik, and E. Kose, “A new and efficient chemoenzymatic route to both enantiomers of alpha ’-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones,”
TETRAHEDRON-ASYMMETRY
, vol. 15, no. 5, pp. 777–781, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57569.