Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction

doi:10.1007/s13659-020-00276-8

应用天然产物 ›› 2021, Vol. 11 ›› Issue (1): 99-103.DOI: 10.1007/s13659-020-00276-8

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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

收稿日期:2020-09-25 修回日期:2020-10-18 出版日期:2021-02-24 发布日期:2021-03-11
通讯作者: Hao Song, Yong Qin
基金资助:
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).

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

Received:2020-09-25 Revised:2020-10-18 Online:2021-02-24 Published:2021-03-11
Contact: Hao Song, Yong Qin
Supported by:
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).

摘要/Abstract

摘要： 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.

关键词: Eburnamine-vincamine alkaloids, Photochemistry, Radical cascade reaction, Johnson-claisen rearrangement

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.

Key words: Eburnamine-vincamine alkaloids, Photochemistry, Radical cascade reaction, Johnson-claisen rearrangement

Yuan Huang, Fanglin Xue, Hengmao Liu, Fei Xue, Xiao-Yu Liu, Hao Song, Yong Qin. Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction[J]. 应用天然产物, 2021, 11(1): 99-103.

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Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction

Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction

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