TY - JOUR
T1 - Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa- 5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator
AU - Falck, J R
AU - Barma, Deb
AU - Mohapatra, Suchismita
AU - Bandyopadhyay, A.
AU - Reddy, Komandla Malla
AU - Qi, Jianjun
AU - Campbell, William
N1 - Funding Information:
The authors express their appreciation to Dr. Raymond E. Conrow for critically reviewing the manuscript. Nancy Spitzbarth and Erik Edwards are thanked for expert technical assistance. Financial support provided by the Robert A. Welch Foundation, NIH (GM 31278, DK38226, HL-37981).
PY - 2004/10/4
Y1 - 2004/10/4
N2 - The four stereoisomers 11,12,15(S)-THETA were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of α,β-dialkoxystannanes 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. 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 α,β- 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.
AB - The four stereoisomers 11,12,15(S)-THETA were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of α,β-dialkoxystannanes 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. 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 α,β- 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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U2 - 10.1016/j.bmcl.2004.07.019
DO - 10.1016/j.bmcl.2004.07.019
M3 - Article
C2 - 15341965
AN - SCOPUS:4444370294
SN - 0960-894X
VL - 14
SP - 4987
EP - 4990
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 19
ER -