Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator.
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.
Falck
J R
JR
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA. j.falck@utsouthwestern.edu
Barma
Deb K
DK
Mohapatra
Suchismita
S
Bandyopadhyay
A
A
Reddy
Komandla Malla
KM
Qi
Jianjun
J
Campbell
William B
WB
D002851:Chromatography, High Pressure Liquid; D004537:Eicosanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004730:Endothelium, Vascular / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D013237:Stereoisomerism; D014665:Vasodilator Agents / Q000138:chemical synthesis* / Q000737:chemistry
D004537:Eicosanoic Acids; D014665:Vasodilator Agents