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 4;14(19):4987-90. doi: 10.1016/j.bmcl.2004.07.019.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Eicosanoic Acids / chemical synthesis*
  • Eicosanoic Acids / chemistry
  • Endothelium, Vascular / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Stereoisomerism
  • Vasodilator Agents / chemical synthesis*
  • Vasodilator Agents / chemistry

Substances

  • Eicosanoic Acids
  • Vasodilator Agents