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CuI-catalyst N-arylation of 4-iodotryptophan derivatives: effort toward the total synthesis of indolactam V

Jing-Qian Jiang, Zheng-Ren Xu, Yan-Xing Jia*   

  1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China
  • Received:2011-10-18 Revised:2012-01-10 Online:2012-03-15 Published:2012-03-15
  • Contact: Yan-Xing Jia*

Abstract:

Efforts toward the total synthesis of indolactam V via CuI-mediated inter- and intra-molecular N-arylation of 4-iodotryptophan derivatives for the introduction of 4-valine moiety from natural L-valine are described. Meanwhile, the efficient synthesis of several pyrroloquinoline derivatives by taking advantage of the CuI-catalyzed intramolecular N-arylation reaction of 4-iodotryptophan is disclosed.

Key words: Intermolecular N-arylation, CuI catalyst, Pyrroloquinoline derivatives, Indolactam V

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