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

DEMİR, AYHAN; Caliskan, Zerrin; AYDIN, ALİME; Bicer, Isil

doi:10.1016/j.tetasy.2006.01.025

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

Atıf İçin Kopyala

DEMİR A. G., Caliskan Z., AYDIN A. E., Bicer I.

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

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
Hatay Mustafa Kemal Üniversitesi Adresli: Evet

Özet

A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α′-acetoxy and α′-hydroxy-α-methoxy cyclic enones starting from α-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of α′-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. © 2006 Elsevier Ltd. All rights reserved.