ARTICLES

A Concise Biogenetically Inspired Formal Synthesis of Camptothecin

  • Yuanzhi Li ,
  • Mengqian Zhu ,
  • Liang Xu
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  • Key Laboratory of Drug Targeting, Ministry of Education, and Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu 610041
* Corresponding author. E-mail:

Received date: 2021-02-20

  Revised date: 2021-03-04

  Online published: 2021-03-25

Supported by

National Natural Science Foundation of China(21871190)

Abstract

A concise biogenetically inspired formal synthesis of camptothecin without use of protecting groups has been developed starting from tryptamine and easily prepared ethyl glutaconaldehyde salt. The synthesis features the key Pictet-Spengler reaction, efficient intramolecular oxa-Diels-Alder reaction to construct heptacyclic monoterpenoid indole alkaloid intermediate, as well as the following Winterfeldt biomimetic oxidation to form quinolinone moiety from indole skeleton.

Cite this article

Yuanzhi Li , Mengqian Zhu , Liang Xu . A Concise Biogenetically Inspired Formal Synthesis of Camptothecin[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2885 -2890 . DOI: 10.6023/cjoc202102034

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