Palladium-catalyzed modular biomimetic synthesis of lignans derivatives

IF 9.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chinese Chemical Letters Pub Date : 2025-02-22 DOI:10.1016/j.cclet.2025.110969

Junlong Tang, Yuhan Zhao, Yangbin Jin, Liren Zhang, Yuanfang Wang, Wanqing Wu, Huanfeng Jiang

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Abstract

Lignans have been established as a privileged scaffold in drug discovery, particularly in anticancer and antioxidant properties. Concise and efficient construction of lignans and their derivatives in a single operation holds great medicinal significance for structure-activity relationship studies yet remains challenging. Drawing inspiration from the biosynthesis of lignans, we present a general, high-step-economy palladium-catalyzed reaction that converts simple chemical feedstocks into dehydrodibenzylbutyrolactone lignans through the in-situ construction and coupling of two phenylpropanoid molecules. The diversity of organoboronic acids and the editability of enyne provide a powerful platform for the rapid construction of lignan libraries, featuring 82 lignans analogs, collective syntheses of 10 distinct lignan skeletons, and 13 hybrid molecules combining pharmacophore fragments with drug and derivatives. The subtle combination of phosphine ligands with quinones for switching chemoselectivity is vital to the success of this protocol.

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钯催化木脂素衍生物的模块化仿生合成

木脂素已被确立为药物发现的特殊支架，特别是在抗癌和抗氧化性能方面。在一次操作中简洁高效地构建木脂素及其衍生物对构效关系的研究具有重要的医学意义，但仍具有挑战性。从木脂素的生物合成中获得灵感，我们提出了一种通用的、高阶经济的钯催化反应，通过原位构建和偶联两个苯丙类分子，将简单的化学原料转化为脱氢二苄基丁内酯木脂素。有机硼酸的多样性和酶的可编辑性为木脂素文库的快速构建提供了强大的平台，包括82种木脂素类似物，10种不同木脂素骨架的集合合成，以及13种将药效团片段与药物及其衍生物结合的杂化分子。膦配体与醌的微妙结合对切换化学选择性至关重要，这一方案的成功。

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来源期刊

Chinese Chemical Letters 化学-化学综合

CiteScore

14.10

自引率

15.40%

发文量

8969

审稿时长

1.6 months

期刊介绍： Chinese Chemical Letters (CCL) (ISSN 1001-8417) was founded in July 1990. The journal publishes preliminary accounts in the whole field of chemistry, including inorganic chemistry, organic chemistry, analytical chemistry, physical chemistry, polymer chemistry, applied chemistry, etc.Chinese Chemical Letters does not accept articles previously published or scheduled to be published. To verify originality, your article may be checked by the originality detection service CrossCheck.