生源启发下的喜树碱的简洁形式合成  

A Concise Biogenetically Inspired Formal Synthesis of Camptothecin

作　　者：李远志[1] 朱孟倩 徐亮[1] Li Yuanzhi;Zhu Mengqian;Xu Liang(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)

机构地区：[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

出　　处：《有机化学》2021年第7期2885-2890,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21871190)资助项目.

摘　　要：以色胺和方便易得的乙基戊烯二醛盐为起始物,以简洁的步骤(最终实现喜树碱全合成共9步反应)完成了喜树碱的生源启发下的无保护基形式合成.合成路线涉及关键的Pictet-Spengler反应,分子内氧杂Diels-Alder反应高效构建单萜吲哚中间体,以及Winterfeldt高效仿生氧化吲哚合成喹啉酮结构.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.

关 键 词：喜树碱 Pictet-Spengler反应 氧杂Diels-Alder反应 Winterfeldt氧化 形式合成 

分 类 号：O629.3[理学—有机化学]