陈立华, 谢蓝, 谢晶曦. 五味子醇甲类似物的全合成J. 药学学报, 1991, 26(1): 20-24.
引用本文: 陈立华, 谢蓝, 谢晶曦. 五味子醇甲类似物的全合成J. 药学学报, 1991, 26(1): 20-24.
LH Chen, L Xie , JX Xie, . TOTAL SYNTHESIS OF AN ANALOGUE OF SCHIZANDRINJ. Acta Pharmaceutica Sinica, 1991, 26(1): 20-24.
Citation: LH Chen, L Xie , JX Xie, . TOTAL SYNTHESIS OF AN ANALOGUE OF SCHIZANDRINJ. Acta Pharmaceutica Sinica, 1991, 26(1): 20-24.

五味子醇甲类似物的全合成

TOTAL SYNTHESIS OF AN ANALOGUE OF SCHIZANDRIN

  • 摘要: 五味子醇甲类似物9是五味子醇甲的代谢产物之一。本文以没食子酸为原料,经甲基化,Henry缩合、还原和分子间还原偶合等六步反应得到了具有苏、赤式两种构型的中间体7,再经DDQ作试剂的非酚氧化偶合反应完成了化合物9的全合成。同时得到另一新化合物10,并对两种产物的生成机制作了探讨。药理结果表明:化合物9具有与五味子醇甲相当的抗惊活性.

     

    Abstract: A schizandrin analogue 9,1,2,3, 10, 11,12-hexamethoxy-6, 7-dihydroxy-cis-6, 7-dimethyl dibenzocyclooctadiene, is one of the metabolites of schizandrin with comparable anti-convulsion activity. In this paper, compound 9 was synthesized from gallic acid through the following sequence of reactions: methylation, Henry condensation, reduction with Fe—FeCl3—HCl, intermolecular reductive coupling and intramolecular nonphenolic oxidative coupling, totally in seven steps. The intermediate 1, 4-diaryl-2, 3-dimethyl-2, 3-butanediol (7) which is a mixture of erythro and threo isomers was converted by DDQ in TFA into compound 9 and another new compound 10 via a different reaction path.

     

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