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

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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

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.