Sun Hong-Yi, Xiao Chun-Fen, Cai Yu-Chen, Chen Yu, Wei Wen, Liu Xian-Ke, Lv Ze-Liang, Zou Yong
Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, PR China.
Chem Pharm Bull (Tokyo). 2010 Nov;58(11):1492-6. doi: 10.1248/cpb.58.1492.
The practical synthesis of important natural polyphenolic stilbenes, including resveratrol, piceatannol and oxyresveratrol, through Perkin methodology is described. Starting from 3,5-dihydoxyacetophenone (1), the common intermediate 3,5-dimethoxyphenylacetic acid (3) can be obtained via methylation and Willgerodt-Kindler reaction. Perkin condensations between (3) and substituted phenylaldehydes 4 furnished E-2,3-diarylacrylic acids 5, followed by decarboxylation in Cu/quinoline giving stilbene intermediates 6 which bear the Z-configuration. Finally, through a simultaneous demethylation/isomerization process in AlI₃/CH₃CN system, the target compounds 7a-c can be obtained respectively in good to high overall yields. The synthetic method proved to be more concise, trans-specific, mild, economical and commonly applicable.
本文描述了通过珀金法实际合成重要的天然多酚芪类化合物，包括白藜芦醇、皮卡特醇和氧化白藜芦醇。从3,5-二羟基苯乙酮（1）开始，通过甲基化和威尔格罗德-金德勒反应可得到常见中间体3,5-二甲氧基苯乙酸（3）。（3）与取代苯甲醛4之间的珀金缩合反应生成E-2,3-二芳基丙烯酸5，随后在铜/喹啉中脱羧得到具有Z构型的芪中间体6。最后，通过在AlI₃/CH₃CN体系中同时进行脱甲基/异构化过程，可分别以良好至高的总收率得到目标化合物7a-c。该合成方法被证明更简洁、具有反式特异性、温和、经济且普遍适用。
