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

Demir A., Findik H., Kose E.

TETRAHEDRON-ASYMMETRY, cilt.15, sa.5, ss.777-781, 2004 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 15 Sayı: 5
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1016/j.tetasy.2003.12.006
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.777-781
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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. (C) 2003 Elsevier Ltd. All rights reserved.