A concise palladium-catalyzed carboamination route to (+/-)-tylophorine

The Journal of Organic Chemistry
Lana M RossiterR Jason Herr

Abstract

A total synthesis of the racemic natural product tylophorine [(+/-)-1] has been demonstrated using the palladium-catalyzed carboamination method developed by Wolfe and co-workers. 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.

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Citations

Mar 20, 2010·The Journal of Organic Chemistry·Brandon R RosenJohn P Wolfe
Jul 13, 2012·The Journal of Organic Chemistry·Günther LahmTill Opatz
Sep 6, 2012·The Journal of Organic Chemistry·Bo SuQingmin Wang
Sep 29, 2015·The Journal of Organic Chemistry·Ashish ThakurJanis Louie
Jan 23, 2016·Organic & Biomolecular Chemistry·Cintia Anton-TorrecillasJose C Gonzalez-Gomez
Apr 11, 2014·Angewandte Chemie·Zhongda PanChristopher J Douglas
Jul 22, 2014·Chemistry : a European Journal·Kathrin WehmingSiegfried R Waldvogel
Jul 30, 2014·Organic & Biomolecular Chemistry·Cintia Anton-Torrecillas, Jose C Gonzalez-Gomez

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