Biomimetic Total Synthesis of Horsfiequinone B Enabled by a Friedel-Crafts Alkylation-Type Non-homodimerization

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-07-29 DOI:10.1039/d4qo00990h

Lumin Li, Ruiling Liu, Rui Yang, Hanwei Li, Ya Liu, Rui Zhan, Wen-Jing Wang, Li-Dong Shao, Dashan Li

引用次数: 0

Abstract

The first and biomimetic total synthesis of horsfiequinone B was achieved in 13 steps. The synthesis features two pivotal transformations, involving Brønsted acid-catalyzed Friedel-Crafts alkylation type non-homodimerization and [Cu(CH3CN)4]PF6/DBED-catalyzed C(sp2)–H aerobic oxidation. Notably, the developed methodology of dimerization enabled the diverse syntheses of other dimeric diarylpropane analogues, and facilitated the further investigations on structure-activity relationship and in-depth bioactivity.

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通过 Friedel-Crafts 烷基化类型的非同二聚化实现贺妃醌 B 的仿生全合成

通过 13 个步骤，首次实现了辣根醌 B 的仿生物全合成。该合成具有两个关键的转化过程，包括布氏酸催化的弗里德尔-卡夫斯烷基化型非同二聚化和[Cu(CH3CN)4]PF6/DBED催化的C(sp2)-H有氧氧化。值得注意的是，所开发的二聚化方法促成了其他二聚二元丙烷类似物的多样化合成，并促进了对结构-活性关系和深度生物活性的进一步研究。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.