ENANTIOSELECTIVE SYNTHESIS OF S-1452, AN ORALLY ACTIVE POTENT THROMBOXANE-A2 RECEPTOR ANTAGONIST

被引:55
作者
OHTANI, M
MATSUURA, T
WATANABE, F
NARISADA, M
机构
[1] Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku
关键词
D O I
10.1021/jo00006a030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and extremely practical enantioselective fission of pro-chiral bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride was applied to the asymmetric synthesis of the potent and orally active thromboxane A2 (TXA2) receptor antagonist, S-1452. The lithium salt of (R)-(-)-benzylmandelate was employed as a chiral ligand, giving a crystalline key intermediate 3 of which the chemical purity was 100.0% after crystallization. Epimerization and the methanolysis process of 3 afforded the half ester 4, which was transformed into S-1452.
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页码:2122 / 2127
页数:6
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