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通过光氧化还原催化异喹啉与芳基重氮盐的直接C-H芳基化实现的甲萘醌和二氢异紫堇碱C的全合成。

Total syntheses of menisporphine and daurioxoisoporphine C enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium salt.

作者信息

Zhang Jing, Chen Jie, Zhang Xiaoyun, Lei Xiaoguang

机构信息

School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, China.

出版信息

J Org Chem. 2014 Nov 7;79(21):10682-8. doi: 10.1021/jo5020432. Epub 2014 Oct 24.

Abstract

Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.

摘要

异喹啉生物碱因其多样的化学结构以及显著的生物活性而成为引人关注的天然产物。在此,我们报道了通过异喹啉核心与芳基重氮盐的温和且高效的光氧化还原催化直接C-H芳基化反应,实现了两种异喹啉生物碱——裂叶紫堇碱和二氢异紫堇碱C的简洁全合成。这种新策略是对传统异喹啉合成方法的补充,将为我们提供一种有用的手段,以实现更具汇聚性和灵活性的方法来获取多样的异喹啉结构。

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