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铜催化的4-碘色氨酸衍生物的N-芳基化反应及其在Indolactam V全合成中的应用

江静倩, 徐正仁, 贾彦兴*   

  1. 北京大学医学部 天然药物及仿生药物国家重点实验室; 药学院 药物化学系, 北京 100191
  • 收稿日期:2011-10-18 修回日期:2012-01-10 出版日期:2012-03-15 发布日期:2012-03-15
  • 通讯作者: 贾彦兴*

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*

摘要: 本文研究了通过CuI 催化的分子内和分子间4-碘色氨酸衍生物的N-芳基化反应引入天然产物indolactam V 的缬氨酸片段, 以完成其全合成, 发现4-碘色氨酸的分子内反应生成了吡咯并喹啉衍生物。

关键词: 分子内的N-芳基化, CuI催化, 吡咯并喹啉衍生物, Indolactam V

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

中图分类号: 

Supporting:

Foundation items: National Natural Science Foundation of China (Grant No. 20802005 and 20972007); the National Basic Research Program of China (973 Program, Grant No. 2010CB833200).
*Corresponding author. Tel.: 86-10-82805166