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(E)-脱氢二聚白藜芦醇-11,11′,13,13′-四甲醚的全合成
Total Synthesis of Resveratrol (E)-dehydrodimer-11,11’,13,13’-tetramethyl Ether
【摘要】 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、13C NMR、IR、H RMS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%。
【Abstract】 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,13C 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%.
【Key words】 resveratrol; oxidative coupling; dimeric stilbenoid; resveratrol (E)-dehydrodimer tetramethyl-ether;
- 【文献出处】 应用化学 ,Chinese Journal of Applied Chemistry , 编辑部邮箱 ,2009年10期
- 【分类号】TQ245
- 【被引频次】3
- 【下载频次】166