A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy and alpha '-hydroxy-alpha-methoxy cyclic enones

Date

2006-03-06

Author

Demir, Ayhan Sıtkı
Caliskan, Z
Aydin, AE
Bicer, I

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A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP afforded (+)-4b and (-)-3b in high enantiomeric excesses (91-94%) and good chemical yields. (c) 2006 Elsevier Ltd All rights reserved.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/57472

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2006.01.025

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, Z. Caliskan, A. Aydin, and I. Bicer, “A new and efficient chemoenzymatic route to both enantiomers of alpha ‘-acetoxy and alpha ’-hydroxy-alpha-methoxy cyclic enones,” TETRAHEDRON-ASYMMETRY, pp. 786–791, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57472.