(E)-脱氢二聚白藜芦醇-11,11′,13,13′-四甲醚的全合成

摘要

The total synthesis of the title compound 10 was accomplished from 3,5-dimethoxybenzoic acid(1) and p-hydroxybenzaldehyde(6). In the process, esterification, reduction, bromination and Wittig-Horner reaction were performed. Compound 5 was then synthesized in a high yield. Treatment of compound 5 with the protection product of compound 6 afforded the key compound 8. The target compound 10 was successfully synthesized through deprotection and bionic oxidative coupling. The structure of compound 10 was confirmed by ~1H NMR, ~(13)C NMR, IR, and HRMS. In conclusion, resveratrol (E)-dehydrodimer-11,11′,13,13′-tetramethyl ether was synthesized through the new method in a total yield of 48.93%.%以3,5-二甲氧基苯甲酸(1)为起始原料, 经过甲醇酯化、氢化铝锂还原、四溴化碳溴代和Wittig-Horner反应,高产率的合成了Wittig-Horner试剂(5). 化合物5与对羟基苯甲醛(6)的羟基保护产物(7)偶联得到化合物(8),后者经去甲氧基亚甲基保护和仿生氧化偶联反应成功地全合成了(E)-脱氢二聚白藜芦醇-11,11′,13,13′-四甲醚(10). 通过~1H NMR、~(13)C NMR、IR、HRMS等测试技术确定化合物10为二聚芪类化合物(E)-脱氢二聚白藜芦醇-11,11′,13,13′-四甲醚,总收率48.93%.