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

Demir A., Caliskan Z., Aydin A., Bicer I.

TETRAHEDRON-ASYMMETRY, vol.17, pp.786-791, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tetasy.2006.01.025
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.786-791
  • Yıldız Technical University Affiliated: Yes

Abstract

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.