Regio- and Diastereo-Selective Biomimetic Synthesis of (+/-)-ε-Viniferin by NIS and Resveratrol

In this work, we describe the synthesis of (±)-permethylated-ϵ-viniferin from resveratrol by successive iodination, methylation and dehalogenation reactions. Iodination reaction by N-iodosuccinimide (NIS) was studied to optimize and confirm a proposed radical mechanism. Switching to acetyl protecting group, a new straightforward regio- and diastereo-selective biomimetic synthesis of (±)-ϵ-viniferin was obtained. Permethylated and free ϵ-viniferin were isolated up to 20 %yield.