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石培琪, 蓝晓茹, 林铮华, 陈创发, 黎旭彬, 叶连宝. 黄绵马酸AB的合成[J]. 中国药科大学学报, 2020, 51(3): 295-298. DOI: 10.11665/j.issn.1000-5048.20200306
引用本文: 石培琪, 蓝晓茹, 林铮华, 陈创发, 黎旭彬, 叶连宝. 黄绵马酸AB的合成[J]. 中国药科大学学报, 2020, 51(3): 295-298. DOI: 10.11665/j.issn.1000-5048.20200306
SHI Peiqi, LAN Xiaoru, LIN Zhenghua, CHEN Chuangfa, LI Xubin, YE Lianbao. Synthesis of flavaspidic acid AB[J]. Journal of China Pharmaceutical University, 2020, 51(3): 295-298. DOI: 10.11665/j.issn.1000-5048.20200306
Citation: SHI Peiqi, LAN Xiaoru, LIN Zhenghua, CHEN Chuangfa, LI Xubin, YE Lianbao. Synthesis of flavaspidic acid AB[J]. Journal of China Pharmaceutical University, 2020, 51(3): 295-298. DOI: 10.11665/j.issn.1000-5048.20200306

黄绵马酸AB的合成

Synthesis of flavaspidic acid AB

  • 摘要: 黄绵马酸AB是香鳞毛蕨中具有多种生物活性的双环型间苯三酚衍生物。对黄绵马酸AB采用逆合成分析法进行结构分析,利用拼合原理设计合成了黄绵马酸AB。以间苯三酚为原料,经维尔斯迈尔-哈克反应、还原反应和酰基化反应合成2-甲基-4-丁酰基间苯三酚,经酰基化反应、烷基化反应和脱酰基反应合成绵马酸片段,最后以N, N-二甲基亚甲基碘化铵活化反应得到黄绵马酸AB。中间体和黄绵马酸AB经MS、1H NMR和13C NMR进行结构确证,目标产物总收率达14.7%,设计的黄绵马酸AB合成路线原料易得且操作简便。

     

    Abstract: Flavaspidic acid AB is a bicyclic phloroglucinol derivative with various biological activities in Dryopteris fragrans (L.) Schott. The structure of flavaspidic acid AB was analyzed by inverse synthesis techniques, and its synthesis was designed under the principle of association. Using phloroglucinol as raw material, the 2-methyl-4-butyrylphloroglucinol was synthesized by Vilsmeier-Haack reaction, reduction and acylation, and the flavaspidic acid fragment was synthesized by acylation, alkylation and deacylation, after which N, N-dimethylmethyleneammonium iodide was activated and the flavaspidic acid AB was obtained. The structures of intermediates and flavaspidic acid AB were confirmed by MS, 1H NMR and 13C NMR, and the yield of the target product reached 14.7%. Results indicate that the designed synthetic route of flavaspidic acid AB is simple and easy.

     

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