Monday, October 21, 2013

Highly Enantioselective Bromocyclization of Tryptamines and Its Application in the Synthesis of (−)-Chimonanthine

by Weiqing Xie,* Guangde Jiang, Huan Liu, Jiadong Hu, Xixian Pan, Hui Zhang, Xiaolong Wan*, Yisheng Lai, Dawei Ma*

Thumbnail image of graphical abstract

A shorter path: A highly enantioselective bromocyclization of tryptamine has been developed using an anionic chiral phase-transfer catalyst. This method provides a direct approach for preparing chiral 3-bromopyrroloindoline from tryptamine, which enables a four-step enantioselective synthesis of (−)-chimonanthine. PG=protecting group.

Angewandter Chemie International Edition
DOI: 10.1002/anie.201306774

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