Chemoenzymatic synthesis of optically active γ-alkyl-γ-butenolides

被引：25
|
作者：
Fujii, Mikio
Fukumura, Motonori
Hori, Yumiko
Hirai, Yasuaki
Akita, Hiroyuki
Nakamura, Kaoru
Toriizuka, Kazuo
Ida, Yoshiteru
机构：
[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan
[2] Toho Univ, Sch Pharmaceut Sci, Chiba 2748510, Japan
[3] Kyoto Univ, Inst Chem Res, Kyoto 61000011, Japan
[4] Yokohama Coll Pharm, Totsuka Ku, Yokohama, Kanagawa 2450066, Japan
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 15期
关键词：
D O I：
10.1016/j.tetasy.2006.08.001
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
rac-Hept-1-en-3-ol 4 was subjected to an enantioselective esterification in the presence of Novozyme 435 and vinyl crotonate as the acyl donor to give (3S)-oct-1-en-3-yl crotonate 7 in > 99% ee and (3R)-alcohol 4 in 99% ee. The E-value of this enzymatic reaction was found to be > 1000. The (S)-crotonic ester 7 was converted by ring-closing metathesis (RCM) using Grubbs' catalyst to give (S)-oct-2-en-4-olide 1 in 96% yield while keeping the high enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2292 / 2298
页数：7
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