常俊标, 谢晶曦. 中药五味子中活性物质的化学研究──五味子醇甲的全合成J. 药学学报, 1998, 33(6): 424-428.
引用本文: 常俊标, 谢晶曦. 中药五味子中活性物质的化学研究──五味子醇甲的全合成J. 药学学报, 1998, 33(6): 424-428.
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Chang Junbiao, Xie Jingxi. TOTAL SYNTHESIS OF SCHIZANDRIN, THE MAIN ACTIVE INGREDIENT ISOLATED FROM THE CHINESE HERBAL MEDICINE FRUCTUS SCHIZANDRAEJ. Acta Pharmaceutica Sinica, 1998, 33(6): 424-428.
Citation: Chang Junbiao, Xie Jingxi. TOTAL SYNTHESIS OF SCHIZANDRIN, THE MAIN ACTIVE INGREDIENT ISOLATED FROM THE CHINESE HERBAL MEDICINE FRUCTUS SCHIZANDRAEJ. Acta Pharmaceutica Sinica, 1998, 33(6): 424-428.
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中药五味子中活性物质的化学研究──五味子醇甲的全合成

TOTAL SYNTHESIS OF SCHIZANDRIN, THE MAIN ACTIVE INGREDIENT ISOLATED FROM THE CHINESE HERBAL MEDICINE FRUCTUS SCHIZANDRAE

    摘要
  • 摘要: 本文以没食子酸为原料进行还原偶合及脱水反应生成顺、反1,4-二(3,4,5-三甲氧基苯基)-2,3-二甲基-2-丁烯化合物(7)。将其进行硼氢化反应,然后分别与2,3-二氯-5,6-二氰-1,4-苯醌(DDQ)和三氟醋酸铊(TTFA)在三氟醋酸(TFA)中进行非酚氧化偶合反应合成了中药五味子中活性化学成分五味子醇甲外消旋体,即(αRS)1,2,3,10,11,12-六甲氧基-6,7-二甲基-6-羟基-5,6,7,8-四氢二苯骈a,c环辛烯(9)。元素分析,MS,UV,IR及NMR光谱数据均与天然五味子醇甲相符。

     

    Abstract: In this paper,schizandrin(9), the main active ingredient isolated from Schisandra chinensis, was synthesized from gallic acid by a new route. This route consists of only nine steps,including reductive-coupling reaction of compound(5) and dehydryoxylatic reaction of compound(6) to give compounds(7Z,7E). By hydroboration, compound (8) was obtained from compound(7Z). With the presence of thallium trifluoroacetate(TTFA) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) compound(9) is obtained from compound(8) by intramolecular nonphenolic oxidative coupling. These compounds were identified by elemental analysis, MS,UV, IR and NMR spectra.

     

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