Use of lipase-catalyzed kinetic resolution for the enantioselective approach toward sesquiterpenes containing quaternary centers: the cuparane family

被引:17
作者
Acherar, S
Audran, G
Vanthuyne, N
Monti, H [1 ]
机构
[1] Fac Sci & Tech St Jerome, Lab React Organ Select, UMR 6516, F-13397 Marseille 20, France
[2] Fac Sci & Tech St Jerome, Lab Stereochim Dynam & Chiralite, ENSSPICAM, UMR 6516, F-13397 Marseille 20, France
关键词
D O I
10.1016/S0957-4166(03)00445-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The enzymatic kinetic resolution of a suitable hydroxylated precursor of the deoxygenated molecule 3, a key intermediate in a synthesis of the cuparane skeleton, was investigated by screening a range of lipases for enantioselective transesterification with vinyl acetate. CAL-B proved to be the best lipase, affording both enantiomers in high enantiomeric excess (>98% ee). Single-crystal X-ray diffraction analysis enabled assignment of the absolute configuration and the enantiospecificity of the tested lipases. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码:2413 / 2418
页数:6
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