Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2885-2890.DOI: 10.6023/cjoc202102034 Previous Articles     Next Articles

ARTICLES

生源启发下的喜树碱的简洁形式合成

李远志, 朱孟倩, 徐亮*()   

  1. 四川大学华西药学院 天然药物系暨教育部靶向药物重点实验室 成都 610041
  • 收稿日期:2021-02-20 修回日期:2021-03-04 发布日期:2021-03-25
  • 通讯作者: 徐亮
  • 基金资助:
    国家自然科学基金(21871190)

A Concise Biogenetically Inspired Formal Synthesis of Camptothecin

Yuanzhi Li, Mengqian Zhu, Liang Xu()   

  1. 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
  • Received:2021-02-20 Revised:2021-03-04 Published:2021-03-25
  • Contact: Liang Xu
  • Supported by:
    National Natural Science Foundation of China(21871190)

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.

Key words: Camptothecin, Pictet-Spengler reaction, oxa-Diels-Alder reaction, Winterfeldt oxidation, formal synthesis