Medical College of Wisconsin
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Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator. Bioorg Med Chem Lett 2004 Oct 04;14(19):4987-90

Date

09/03/2004

Pubmed ID

15341965

DOI

10.1016/j.bmcl.2004.07.019

Scopus ID

2-s2.0-4444370294 (requires institutional sign-in at Scopus site)   21 Citations

Abstract

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 dialkylthionocarbamates 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.

Author List

Falck JR, Barma DK, Mohapatra S, Bandyopadhyay A, Reddy KM, Qi J, Campbell WB

Author

William B. Campbell PhD Professor in the Pharmacology and Toxicology department at Medical College of Wisconsin




MESH terms used to index this publication - Major topics in bold

Chromatography, High Pressure Liquid
Eicosanoic Acids
Endothelium, Vascular
Gas Chromatography-Mass Spectrometry
Stereoisomerism
Vasodilator Agents