A new and efficient chemoenzymatic route to both enantiomers of a-acetoxy and a-hydroxy-a-methoxy cyclic enones
Yükleniyor...
Tarih
2006
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
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.
Açıklama
Anahtar Kelimeler
Manganese(Iii) Acetate, Stereoselective Synthesis, Asymmetric-Synthesis, Oxidation, Combination, Derivatives, Acyloxy, Ketones, Diosphenols, Acid
Kaynak
Tetrahedron-Asymmetry
WoS Q Değeri
Q2
Scopus Q Değeri
N/A
Cilt
17
Sayı
5
