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, cilt.17, sa.5, ss.786-791, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17 Sayı: 5
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1016/j.tetasy.2006.01.025
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.786-791
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.