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

F Zhang, S Zaidi, KM Haney, GE Kellogg…

Index: Zhang, Feng; Zaidi, Saheem; Haney, Kendra M.; Kellogg, Glen E.; Zhang, Yan Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 7945 - 7952

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Citation Number: 13

Abstract

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.