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A Homo-Mannich Reaction Strategy Enables Collective Access to Ibophyllidine,Aspidosperma, Kopsia,and Melodinus Alkaloids |
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| Authors: | Dan Jiang Peng Tang Hongbing Xiong Shuai Lei Yulian Zhang Chongzhou Zhang Ling He Hanyue Qiu Prof Dr Min Zhang |
| Institution: | 1. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing 401331 China
Contribution: Investigation (lead), Methodology (lead), Writing - review & editing (lead);2. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing 401331 China Contribution: Investigation (supporting);3. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing 401331 China Contribution: Writing - review & editing (supporting);4. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba, Chongqing 401331 China |
| Abstract: | We report here a homo-Mannich reaction of cyclopropanol with an iminium ion, generated by an asymmetric allylic dearomatization of indole, to construct a tricyclic hydrocarbazole core, which is shared by a variety of monoterpenoid indole alkaloids across families. Through this approach, an all-carbon quaternary stereogenic center as well as an allyl and a ketone group were installed. Using this functionalized hydrocarbazole as the structural platform, D ring and E rings of different sizes (i.e., five-, six-, and seven-membered) were successively or simultaneously assembled, leading to a collective asymmetric synthesis of seven alkaloids belonging to the ibophyllidine, Aspidosperma, Kopsia, and Melodinus alkaloid families. |
| Keywords: | Alkaloids Cyclopropanol Homo-Mannich Reaction Natural Products Total Synthesis |