Regio- and stereoselective syntheses of the natural product CCR5 antagonist anibamine and its three olefin isomers.

Feng Zhang, Saheem Zaidi, Kendra M Haney, Glen E Kellogg, Yan Zhang

Department of Medicinal Chemistry, Virginia Commonwealth University, 800 East Leigh Street, Richmond, Virginia 23298, United States.

The Journal of organic chemistry 2011 Oct 7

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The syntheses of the natural product anibamine and its three olefin isomers have been achieved concisely and efficiently via highly regio- and stereoselective reactions. The crucial steps included a regioselective palladium-catalyzed alkynylation by Sonogashira coupling and a stereoselective Suzuki coupling. Further conformation analyses and in vitro calcium mobilization studies were carried out to characterize the compounds' biological properties.

Citation

Feng Zhang, Saheem Zaidi, Kendra M Haney, Glen E Kellogg, Yan Zhang. Regio- and stereoselective syntheses of the natural product CCR5 antagonist anibamine and its three olefin isomers. The Journal of organic chemistry. 2011 Oct 7;76(19):7945-52