| SHORT COMMUNICATION |
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Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction |
| Yuan Huang, Fanglin Xue, Hengmao Liu, Fei Xue, Xiao-Yu Liu, Hao Song, Yong Qin |
| Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, Sichuan, China |
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Abstract An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visiblelight photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter.
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| Keywords
Eburnamine-vincamine alkaloids
Photochemistry
Radical cascade reaction
Johnson-claisen rearrangement
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| Fund:We are grateful for the financial surpport from National Natural Science Foundation of China (21921002 and 21991114) and National Science and Technology Major Projects for “Major New Drugs Innovation and Development” (2018ZX09711003-015 and 2018ZX09711001-005-004). |
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Corresponding Authors:
Hao Song, Yong Qin
E-mail: songhao@scu.edu.cn;yongqin@scu.edu.cn
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Issue Date: 11 March 2021
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