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.
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—FeCl_3—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.
出处
《药学学报》
CAS
CSCD
北大核心
1991年第1期20-24,共5页
Acta Pharmaceutica Sinica
关键词
五味子醇甲
类似物
合成
Dibenzocyclooctadiene lignan
Nonphenolic oxidative coupling
Schizandrin' analogue
Total synthesis
