Literature DB >> 15341965

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 Falck1, Deb K Barma, Suchismita Mohapatra, A Bandyopadhyay, Komandla Malla Reddy, Jianjun Qi, William B Campbell.   

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.

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Year:  2004        PMID: 15341965     DOI: 10.1016/j.bmcl.2004.07.019

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  8 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Synthesis of enantioenriched alpha-(hydroxyalkyl)-tri-n-butylstannanes.

Authors:  Anyu He; John R Falck
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.

Authors:  Hao Li; Anyu He; John R Falck; Lanny S Liebeskind
Journal:  Org Lett       Date:  2011-06-15       Impact factor: 6.005

4.  Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides.

Authors:  J R Falck; Paresh K Patel; Anish Bandyopadhyay
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

5.  Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters.

Authors:  Elizabeth C Swift; Elizabeth R Jarvo
Journal:  Tetrahedron       Date:  2013-07-22       Impact factor: 2.457

6.  Role of arachidonic acid lipoxygenase metabolites in acetylcholine-induced relaxations of mouse arteries.

Authors:  Kathryn M Gauthier; Daniel H Goldman; Nitin T Aggarwal; Yuttana Chawengsub; J R Falck; William B Campbell
Journal:  Am J Physiol Heart Circ Physiol       Date:  2010-12-30       Impact factor: 4.733

7.  Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n-butylstannanes with alkenyl, aryl, and heteroaryl electrophiles.

Authors:  Mohan Goli; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-12-09       Impact factor: 6.005

8.  Structural characterization of monohydroxyeicosatetraenoic acids and dihydroxy- and trihydroxyeicosatrienoic acids by ESI-FTICR.

Authors:  Lijie Cui; Marilyn A Isbell; Yuttana Chawengsub; John R Falck; William B Campbell; Kasem Nithipatikom
Journal:  J Am Soc Mass Spectrom       Date:  2008-01-31       Impact factor: 3.109

  8 in total

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