A Concise Palladium-Catalyzed Carboamination Route to (+/-)-Tylophorine

作者:Rossiter Lana M; Slater Meagan L; Giessert Rachel E; Sakwa Samuel A; Herr R Jason*
来源:Journal of Organic Chemistry, 2009, 74(24): 9554-9557.
DOI:10.1021/jo902114u

摘要

A total synthesis of the racemic natural product tylophorine [(+/-)-1] has been demonstrated using the palladium-catalyzed carboamination method developed by Wolfe and coworkers. In this case, an electron-rich aryl bromide 18 was prepared in four steps and subjected to palladium-catalyzed Wolfe carboamination conditions with olefinic carbamate 7 to provide the racemic 2-(arylmethyl)pyrrolidine (+/-)-19 in good yield and was further elaborated to racemic tylophorine. This application of the Wolfe carboamination protocol as a key step to construct a natural product provides further evidence of the utility of the method.

  • 出版日期2009-12-18