Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator

被引：19

作者：

Falck, JR ^{[1
]}

Barma, DK

Mohapatra, S

Bandyopadhyay, A

Reddy, KM

Qi, JJ

Campbell, WB

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

[2] Med Coll Wisconsin, Dept Pharmacol & Toxicol, Milwaukee, WI 53226 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 19期

关键词：

D O I：

10.1016/j.bmcl.2004.07.019

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The four stereoisomers of the endothelial-derived vasorelaxant 11,12,15(S)-trihydroxyeicosatrienoic acid [1, 11,12,15(S)THETA] were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of alpha,beta-dialkoxystannanes with organic electrophiles and the utility of dialkylthionocarbarnates as orthogonal alcohol protective groups. Only 11(R),12(S),15(S)-THETA was comparable to natural material by HPLC, GC/MS, and in vitro bioassay. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4987 / 4990

页数：4

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