白皮杉醇的合成

Synthesis of Piceatannol

以3,4-二甲氧基苄醇为原料,通过溴代、Arbuzov重排反应、Wittig-Horner反应和脱甲基化反应得到目标产物（E）-3,3′,4,5′-四羟基二苯乙烯,即白皮杉醇。该文考察了溴代试剂、Arbuzov重排反应温度、Wittig-Horner反应中溶剂及脱甲基反应试剂等各因素对产物产率的影响,得到最佳反应条件为：以三溴化磷为溴代试剂,Arbuzov重排反应条件为100℃反应1 h,再于120~130℃反应3~4 h,以DMF为Wittig-Horner反应溶剂,无水AlCl3作为脱甲基化试剂。通过IR、1HNMR及13CNMR确定了目标产物的结构。

Starting from the 3,4-dimethoxybenzyl alcohol,3,3′,4,5′-tetrahydroxystilbene（piceatannol） was synthesized through bromation,Arbuzov rearrangement followed by Wittig-Horner reaction and demethylation reaction.The effects of brominating agents,the temperature of Arbuzov rearrangement,solvent in Wittig-Horner reaction,and demethylation agents were investigated.The optimal conditions were： phosphorus tribromide being used as the brominating agent,Arbuzov rearrangement conditions of 100 ℃ for 1 h and then 120～130 ℃ for 3～4 h,dimethylformamide being used as the solvent in Wittig-Horner reaction,dry aluminum chloride being used as the demethylation agent.The structure of the target molecules was confirmed by means of IR,1HNMR and 13CNMR spectra.