Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3126-3133.DOI: 10.6023/cjoc202102006 Previous Articles     Next Articles



高中润, 王媛, 宋航, 徐正仁*(), 贾彦兴*()   

  1. 北京大学药学院 天然药物及仿生药物国家重点实验室 北京 100191
  • 收稿日期:2021-02-01 修回日期:2021-05-02 发布日期:2021-05-25
  • 通讯作者: 徐正仁, 贾彦兴
  • 作者简介:
    † 共同第一作者
  • 基金资助:

Cascade Cyclization Reaction Initiated by Benzylic Carbocation of Indole: Scope and Mechanistic Insights

Zhongrun Gao, Yuan Wang, Hang Song, Zhengren Xu(), Yanxing Jia()   

  1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences,Peking University, Beijing 100191
  • Received:2021-02-01 Revised:2021-05-02 Published:2021-05-25
  • Contact: Zhengren Xu, Yanxing Jia
  • About author:
    † (These authors contributed equally to this work).
  • Supported by:
    National Natural Science Foundation of China(21871013)

During the course of the total synthesis of α-cyclopianic acid (α-CPA) and speradine C, our research group have developed a biomimetic cascade cyclization reaction initiated by the benzylic carbocation of indole. In this paper, the scope and the reaction mechanism of the cascade cyclization reaction were studied. The experimental results show that the cascade cyclization reaction occurrs at the benzylic carbocation of indole, indicating that the conjugation effect of the indole nitrogen atom plays a key role in the cascade cyclization of benzylic carbocations.

Key words: mechanism, cascade cyclization, benzylic carbocation, indole, conjugation effect