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
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.
UR - http://www.scopus.com/inward/record.url?scp=4444370294&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2004.07.019
DO - 10.1016/j.bmcl.2004.07.019
M3 - Article
C2 - 15341965
AN - SCOPUS:4444370294
VL - 14
SP - 4987
EP - 4990
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 19
ER -