白藜芦醇、白皮杉醇和赤松素的合成

Synthesis of Resveratrol,Piceatannol and Pinosylvin

研究了白藜芦醇、赤松素和白皮杉醇的一种简便合成方法.二苯乙烯类化合物在铝和碘的作用下实现双键顺反异构和芳甲醚甲基的脱除,实现白藜芦醇、赤松素和白皮杉醇的高效合成,反应的总收率分别为68%,78%和56%.反应溶剂过滤后可以再次使用.通过量子化学计算和控制实验认为碘自由基可能是脱甲基过程中导致双键顺反异构的关键因素.

A convenient method for the practical synthesis of resveratrol,piceatannol and pinosylvin is described.Resveratrol,pinosylvin and piceatannol can be achieved through a simultaneous demethylation and isomerization process from stilbenes with the aid of aluminum and iodine.The overall yields of the reaction were 68%,78%and 56%(based on aromatic aldehyde).The solvent of the reaction can be reused after filtered.At the same time,quantum chemical calculations and control experiments show that iodine radical may be the key factor leading to cis-trans isomerization of double bond in the process of demethylation.