Practical and efficient total synthetic route of the resveratrol dimer (±)-ε-viniferin

Abstract

A practical and efficient total synthetic route of the resveratrol dimer (±)-ε-viniferin (2) with benzyl as protecting group for phenols was achieved with high overall yield. The synthetic approach involved a palladium-catalyzed direct arylation, triethylsilane-mediated reduction of benzofuran, and selective debenzylation reaction. Selective debenzylation in the presence of reducible and acid-sensitive groups catalyzed using Pd/C and 1,4-cyclohexadiene was implemented to complete the total synthesis.