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.

摘要

以手性白藜芦醇衍生物的酶介导氧化偶联反应为关键步骤，初步探索了白藜芦醇二聚体的不对称仿生合成。辣根过氧化物酶-H ₂ O ₂促进了 11,13-二仲丁基白藜芦醇醚和 3,5-二溴白藜芦醇二仲丁基醚的氧化，生成了 8-5-偶联中间体和几个 8-8 -偶联的二聚体混合物，分别。偶联二聚体的酸催化脱丁基和氢解脱溴合成了具有未确定立体异构体比例的天然 (+)- δ -viniferin 和非天然 (+)-isoquadrangularin A。