title: Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator.
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.
authors.affiliation: Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA. j.falck@utsouthwestern.edu
authors.forename: J R
authors.initials: JR
authors.lastname: Falck
authors.forename: Deb K
authors.initials: DK
authors.lastname: Barma
authors.forename: Suchismita
authors.initials: S
authors.lastname: Mohapatra
authors.forename: A
authors.initials: A
authors.lastname: Bandyopadhyay
authors.forename: Komandla Malla
authors.initials: KM
authors.lastname: Reddy
authors.forename: Jianjun
authors.initials: J
authors.lastname: Qi
authors.forename: William B
authors.initials: WB
authors.lastname: Campbell
mesh_terms: 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
chemical_list: D004537:Eicosanoic Acids; D014665:Vasodilator Agents