Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione

被引：16

作者：

Botes, AL

Harvig, D

van Dyk, MS

Sarvary, I

Frejd, T

Katz, M

Hahn-Hägerdal, B

Gorwa-Grauslund, MF

机构：

[1] Univ Orange Free State, Dept Microbiol & Biochem, ZA-9300 Bloemfontein, South Africa

[2] Lund Univ, Ctr Chem & Chem Engn, Dept Organ & Bioorgan Chem, S-22100 Lund, Sweden

[3] Lund Univ, Ctr Chem & Chem Engn, Dept Appl Microbiol, S-22100 Lund, Sweden

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 08期

关键词：

D O I：

10.1039/b111064k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Yeast strains from more than 31 different genera were screened for the enantioselective reduction of bicyclo[2.2.2]-octane-2,6-dione (1). Reducing activity was found in 80% of the screened yeasts. Bicyclo[2.2.2]octane-2,6-dione was enantioselectively reduced (> 98% ee) to (1R, 4S, 6S)-6-hydroxybicyclo[2.2.2]octane-2-one (-)-2 by 69% of the strains. Enantioselective reduction of the diketone to (1S, 4R, 6S)-6-hydroxybicyclo[2.2.2]octane-2-one ((+)-3, >98% ee) as a major product is reported for the first time. Candida tropicalis UOFS Y-0534 and Candida wickerhamii UOFS Y-0652 displayed this unusual diastereoselectivity.

引用

页码：1111 / 1114

页数：4

共 21 条

[1] Neighboring group participation in a regio- and stereoselective chlorination of a bicyclo[2.2.2]octanone [J].