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银杏酸的合成新方法
引用本文:赵剑阳,王婷,刘情情,朱槿,黄晴菲,王启卫.银杏酸的合成新方法[J].合成化学,2016,24(4):359-361.
作者姓名:赵剑阳  王婷  刘情情  朱槿  黄晴菲  王启卫
作者单位:1. 中国科学院 成都有机化学研究所,四川 成都 610041; 2. 中国科学院大学,北京 100049
基金项目:成都市高新区创新创业人才奖
摘    要:报道了一种合成银杏酸类化合物的新方法。以2-羟基-5-甲基苯甲酸为起始原料,经甲基化和溴代反应后,通过Wittig反应构建不同链长侧链合成了2-甲氧基-6-十三碳-1-烯基苯甲酸甲酯(6a)和2-甲氧基-6-十五碳-1-烯基苯甲酸甲酯(6b);用钯碳氢化还原6中的碳碳双键后脱除甲基合成了两种不同链长银杏酸,总收率分别为46%和40%,其结构经1H NMR和ESI-MS确证。

关 键 词:2-羟基-5-甲基苯甲酸  银杏酸  Wittig反应  脱甲基  药物合成  
收稿时间:2015-11-30

A Novel Synthetic Method for Ginkgolic Acid
ZHAO Jian-yang,WANG Ting,LIU Qing-qing,ZHU Jin,HUANG Qing-fei,WANG Qi-wei.A Novel Synthetic Method for Ginkgolic Acid[J].Chinese Journal of Synthetic Chemistry,2016,24(4):359-361.
Authors:ZHAO Jian-yang  WANG Ting  LIU Qing-qing  ZHU Jin  HUANG Qing-fei  WANG Qi-wei
Institution:1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; 2. University of Chinese Academy of Sciences, Beijing 100049, China
Abstract:A novel method for the synthesis of the ginkgolic acid was reported.2-Methoxy-6-tridec-1-enylbenzoic acid methyl este (6a) and 2-methoxy-6-pentadec-1-enylbenzoic acid methyl ester (6b) were synthesized by methlation, N-bromosuccinimide substitution and constructing different long chain olefins via Wittig reaction from 2-methy-5-hydroxy benzoic acid.Two ginkgolic acids with different long chains were synthesized by reduction of carbon carbon double bond of 6 with palladium carbon then demethylating, the total yield were 46% and 40%, respectively.The structures were confirmed by 1 H NMR and ESI-MS.
Keywords:2-methy-5-hydroxy benzoic acid  ginkgolic acid  Wittig reaction  demethylation  drug synthesis
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