Visible-Light-Promoted Biomimetic Reductive Functionalization of Quaternary Benzophenanthridine Alkaloids,Journal of Natural Products

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Visible-Light-Promoted Biomimetic Reductive Functionalization of Quaternary Benzophenanthridine Alkaloids
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-07-30 , DOI: 10.1021/acs.jnatprod.1c00512
Lin Wang ₁ , Xinhao Wang ₁ , Wei Wang ₁ , Wei Liu _{1,

2} , Yisong Liu _{1,

2} , Hongqi Xie _{1,

2} , Oliver Reiser ₃ , Jianguo Zeng _{1,

2} , Pi Cheng _{1,

2}

Affiliation

Reduction of an iminium C═N double bond is the most important phase I metabolism process associated with the cytotoxic property of quaternary benzophenanthridine alkaloids (QBAs). Inspired by the light-mediated reduction of QBAs with nicotinamide adenine dinucleotide, a visible-light-promoted reductive functionalization reaction of QBAs is reported in this study. C4-Alkyl-1,4-dihydropyridines (DHPs) enable the direct reductive alkylation of QBA independently, serving as both single-electron-transfer reductant reagents under irradiation with 455 nm blue light in the absence of photocatalysts and additional additives. Our protocol can be further applied to the semisynthesis of natural 6-substituted dihydrobenzophenanthridine derivatives such as O-acetyl maclekarpine E.

中文翻译：

四元苯并菲啶生物碱的可见光促进仿生还原功能化

亚胺鎓 C=N 双键的还原是与季苯并菲啶生物碱 (QBA) 的细胞毒性相关的最重要的 I 相代谢过程。受光介导的烟酰胺腺嘌呤二核苷酸还原 QBA 的启发，本研究报道了可见光促进的 QBA 还原功能化反应。C4-烷基-1,4-二氢吡啶 (DHP) 能够独立地对 QBA 进行直接还原烷基化，在没有光催化剂和其他添加剂的情况下，在 455 nm 蓝光照射下用作单电子转移还原剂。我们的协议可以进一步应用于天然 6-取代二氢苯并菲啶衍生物的半合成, 如O-乙酰基麦克卡品 E。

更新日期：2021-08-27

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