ARTICLES

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

  • Zhongrun Gao ,
  • Yuan Wang ,
  • Hang Song ,
  • Zhengren Xu ,
  • Yanxing Jia
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  • State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences,Peking University, Beijing 100191
† (These authors contributed equally to this work).
*Corresponding authors.E-mail: ;

Received date: 2021-02-01

  Revised date: 2021-05-02

  Online published: 2021-05-25

Supported by

National Natural Science Foundation of China(21871013)

Abstract

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.

Cite this article

Zhongrun Gao , Yuan Wang , Hang Song , Zhengren Xu , Yanxing Jia . Cascade Cyclization Reaction Initiated by Benzylic Carbocation of Indole: Scope and Mechanistic Insights[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3126 -3133 . DOI: 10.6023/cjoc202102006

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