FeCl3/KI-Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A,B and Derivatives |
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| Authors: | Ying-Chun Song Ming-Xuan Wang Yun-Ying Yi Yu-Ting Liu Wen-Xin Zhang Zi-Yue Wang Yuan-Yuan Sun An-Xin Wu Yan-Ping Zhu |
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| Affiliation: | 1. School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Shandong, Yantai, 264005 People's Republic of China;2. National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan, 430079 People's Republic of China |
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| Abstract: | A total synthesis strategy was developed for the synthesis of luotonin A, B and their analogues using synergistic FeCl3/KI-catalyzed oxidative cyclization. This protocol utilizes cheap and widely available N-propargyl 2-methyl-quinazolinones and arylamines under mild conditions, and it has a wide substrate scope and high atom economy. Different natural products (luotonin A, B and derivatives) can be synthesized via a unique switchable approach. Further transformations from luotonin B to luotonin E and structural modification of natural products demonstrate the potential applications of this method. Moreover, camptothecin can also be modified with the reported protocol to afford the hydroxyl-substituted product. |
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| Keywords: | Total synthesis Oxidative cyclization Natural products Switchable synthesis Luotonin alkaloids |
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