苄基异喹啉生物碱Neolitacumonine、Mollinedine和Papaverine的全合成

doi:10.6023/cjoc201905045

有机化学 ›› 2020, Vol. 40 ›› Issue (1): 149-155.DOI: 10.6023/cjoc201905045 上一篇下一篇

研究论文

苄基异喹啉生物碱Neolitacumonine、Mollinedine和Papaverine的全合成

孙勉勉^a, 李风雷^a, 何云刚^a, 朱星亮^a, 刘世领^b, 施小新^a

a 华东理工大学药学院上海市化学生物学重点实验室上海 200237;
b 青平药业有限公司上海 201710

收稿日期:2019-05-22 修回日期:2019-08-26 发布日期:2019-09-05
通讯作者: 施小新, 刘世领 E-mail:xxshi@ecust.edu.cn;liushiling@tenrypharm.com
基金资助:
国家自然科学基金（Nos.20972048，20172015）资助项目.

Total Syntheses of Benzylisoquinoline Alkaloids Neolitacumoine, Mollinedine and Papaverine

Sun Mianmian^a, Li Fenglei^a, He Yungang^a, Zhu Xingliang^a, Liu Shiling^b, Shi Xiaoxin^a

a Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237;
b Qingping Pharmaceutical Co., Ltd., Shanghai 201710

Received:2019-05-22 Revised:2019-08-26 Published:2019-09-05
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20972048, 20172015).

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摘要/Abstract

研究了苄基异喹啉生物碱的一条新的通用合成路线.其关键步骤为1-苄基-3，4-二氢异喹啉的铜催化氧化芳构化串联反应.以胡椒醛或3，4-二甲氧基苯甲醛为起始原料，经8步反应，分别以42%、37%和37%的总收率实现了三个苄基异喹啉生物碱Neolitacumonine、Mollinedine和Papaverine的全合成.

关键词: 苄基异喹啉生物碱, Neolitacumonine, Mollinedine, Papaverine

A new general synthetic route towards benzylisoquinoline alkaloids was developed. The key step of this route is Cu-catalyzed cascade oxidation-aromatization of 1-benzyl-3,4-dihydroisoquinolines. The three benzylisoquinoline alkaloids such as neolitacumonine, mollinedine and papaverine were synthesized starting from piperonaldehyde and 3,4-dimethoxybenzaldehyde by 8 steps in 42%, 37% and 37% overall yields, respectively.

Key words: benzylisoquinoline alkaloids, neolitacumonine, mollinedine, papaverine

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孙勉勉, 李风雷, 何云刚, 朱星亮, 刘世领, 施小新. 苄基异喹啉生物碱Neolitacumonine、Mollinedine和Papaverine的全合成[J]. 有机化学, 2020, 40(1): 149-155.

Sun Mianmian, Li Fenglei, He Yungang, Zhu Xingliang, Liu Shiling, Shi Xiaoxin. Total Syntheses of Benzylisoquinoline Alkaloids Neolitacumoine, Mollinedine and Papaverine[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 149-155.

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苄基异喹啉生物碱Neolitacumonine、Mollinedine和Papaverine的全合成

Total Syntheses of Benzylisoquinoline Alkaloids Neolitacumoine, Mollinedine and Papaverine

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