Utilization of Sequential Palladium-Catalyzed Cross-Coupling Reactions in the Stereospecific Synthesis of Trisubstituted Olefins

…, U Nettekoven, A Schnyder, E Bappert…

Index: Houpis, Ioannis N.; Shilds, Didier; Nettekoven, Ulrike; Schnyder, Anita; Bappert, Erhart; Weerts, Koen; Canters, Martine; Vermuelen, Wim Organic Process Research and Development, 2009 , vol. 13, # 3 p. 598 - 606

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Citation Number: 17

Abstract

A stereospecific synthesis of the drug-candidate 1 is described. The synthetic sequence, aimed at accomplishing modularity and cost savings, features a series of organometallic steps to afford stereospecifically the desired trisubstituded olefin active pharmaceutical ingredient. Key developments consist of a mild Sonogashira reaction of aryl bromide 7a with the polymerization prone propargyl alcohol and a stereospecific hydroalumination, Zn/Al ...