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

doi:10.1016/j.bmcl.2004.07.019

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

Institute for Healthy Aging

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

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 language	English
Pages (from-to)	4987-4990
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2004.07.019
State	Published - 4 Oct 2004

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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 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.",

author = "Falck, {J. R.} and Deb Barma and Suchismita Mohapatra and A. Bandyopadhyay and Reddy, {Komandla Malla} and Jianjun Qi and William Campbell",

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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 journal › Article › peer-review

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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

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