Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa- 5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator

J R Falck, Deb Barma, Suchismita Mohapatra, A. Bandyopadhyay, Komandla Malla Reddy, Jianjun Qi, William Campbell

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)4987-4990
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume14
Issue number19
DOIs
StatePublished - Oct 4 2004

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Stereoisomerism
Bioassay
Vasodilator Agents
Biological Assay
Endothelium
Copper
High Pressure Liquid Chromatography
Alcohols
Acids
In Vitro Techniques
11,12,15-trihydroxyeicosatrienoic acid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa- 5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator. / Falck, J R; Barma, Deb; Mohapatra, Suchismita; Bandyopadhyay, A.; Reddy, Komandla Malla; Qi, Jianjun; Campbell, William.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 19, 04.10.2004, p. 4987-4990.

Research output: Contribution to journalArticle

Falck, J R ; Barma, Deb ; Mohapatra, Suchismita ; Bandyopadhyay, A. ; Reddy, Komandla Malla ; Qi, Jianjun ; Campbell, William. / Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa- 5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator. In: Bioorganic and Medicinal Chemistry Letters. 2004 ; Vol. 14, No. 19. pp. 4987-4990.
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