Preliminary exploration on enzyme-promoted asymmetric biomimetic synthesis of resveratrol dimers

Abstract

The asymmetric biomimetic synthesis of resveratrol dimers was preliminarily explored using the enzyme-mediated oxidative coupling reactions of chiral resveratrol derivatives as the key step. The horseradish peroxidase-H2O2-promoted oxidations of 11,13-di-sec-butyl resveratrol ether and 3,5-dibromo-resveratrol di-sec-butyl ethers generated an 8-5-coupled intermediate and several 8-8-coupled dimeric mixtures, respectively. The acid-catalyzed debutylation of the coupling dimers and hydrogenolytic debromination synthesized natural (+)-δ-viniferin and unnatural (+)-isoquadrangularin A with undetermined stereoisomer ratio.