Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator |
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| Authors: | Falck J R Barma Deb K Mohapatra Suchismita Bandyopadhyay A Reddy Komandla Malla Qi Jianjun Campbell William B |
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| Affiliation: | Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA. j.falck@utsouthwestern.edu |
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| 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. |
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