Related Experiment Video
Updated: Sep 7, 2025

Visualizing Lignification Dynamics in Plants with Click Chemistry: Dual Labeling is BLISS!
Published on: January 26, 2018
Taming the radical cation intermediate enabled one-step access to structurally diverse lignans
Jia-Chen Xiang1,2, Cédric Fung1, Qian Wang1
1Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, 1015, Lausanne, Switzerland.
Abstract:
Lignans, in spite of their structural diversity, are all biosynthetically derived from coniferyl alcohol. We report herein a divergent synthesis of lignans from biomass-derived monolignols in a short synthetic sequence. Blue LED irradiation of a dichloromethane solution of dicinnamyl ether derivatives in the presence of Cu(TFA)2, an alcohol (2.0 equiv) and a catalytic amount of Fukuzumi's salt affords the C7-alkoxylated aryltetralin cyclic ethers. Increasing the amount of alcohol under otherwise identical conditions diverts the reaction course to furnish the C7,C7'-dialkoxylated dibenzyltetrahydrofurans, while replacing Cu(TFA)2 with diphenyl disulfide (PhSSPh) provides selectively the C7-monoalkoxylated dibenzyltetrahydrofurans. Aza-, thia- and carba-analogues of lignans are equally accessible by simply changing the tethering atom of the allylic alcohols. Concise total syntheses of aglacins A, E, F, brassilignan, and dehydrodimethylconidendrin are documented featuring these transformations.
More Related Videos
Related Concept Videos
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Radical Chain-Growth Polymerization: Overview
Radical Reactivity: Nucleophilic Radicals
Radical Substitution: Allylic Bromination
Radical Reactivity: Concentration Effects
Radical Reactivity: Intramolecular vs Intermolecular

