Citation: Junlong Tang, Yuhan Zhao, Yangbin Jin, Liren Zhang, Yuanfang Wang, Wanqing Wu, Huanfeng Jiang. Palladium-catalyzed modular biomimetic synthesis of lignans derivatives[J]. Chinese Chemical Letters, ;2025, 36(7): 110969. doi: 10.1016/j.cclet.2025.110969 shu

Palladium-catalyzed modular biomimetic synthesis of lignans derivatives

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China

cewuwq@scut.edu.cn

jianghf@scut.edu.cn

Received Date: 22 December 2024
Revised Date: 7 February 2025
Accepted Date: 17 February 2025
Available Online: 22 February 2025

Figures(6)

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.
- Lignans,
- Palladium,
- Modular synthesis,
- Dicarbofunctionalized cyclization,
- Enyne
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