8-5’新木脂素类化合物的合成方法研究

对羟基桂皮酸甲酯和阿魏酸甲酯分别在氧化银催化下发生自由基仿生氧化偶联反应, 合成得苯并二氢呋喃环结构化合物1, 1经甲基化反应得2. 1a和1和2分别在无水碳酸钾、10%氢氧化钠水溶液等不同的碱性条件下进行反应, 获得了11个苯并二氢呋喃环开环产物, 即8-5’新木脂素类化合物3a～9b, 实现了由苯并二氢呋喃新木脂素向8-5’新木脂素的转变, 也为合成芪类化合物提供了一种新方法. C-8位上的吸电子基团如酯基的影响使苯并二氢呋喃环易在碱性条件下开环形成8-5’新木脂素类化合物．所合成化合物的结构由MS, IR, 1H NMR和13C NMR进行了表征.

Synthesis of 8-5' Neolignan Compounds

Eleven 8-5’ neolignan compounds 3a～9b have been synthesized via reactions of dihydrobenzofuran compounds 1 and 2 with dry K2CO3 or 10% NaOH (aq.) under distinct conditions. 1a and 1b were synthesized from methyl 4-hydroxy cinnamate and methyl ferulate respectively by Ag2O-catalyzed biomi-metic oxidative coupling reaction while 2a and 2b were obtained through methylation of 1a and 1b, respec-tivly Synthesis of compounds 3a～9b not only achieved transformation successfully from dihydrobenzofuran neolignans to 8-5’ neolignans, but also offered a new method for the synthesis of stilbenoids. The effect of 8-electron-withdrawing substituents such as COOCH3 group made transformation smoothly from dihydrobenzofuren neolignans to 8-5’ neolignan compounds. All of these synthesized compounds have been confirmed by MS, IR, 1HNMR and 13CNMR techniques.