Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation
Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation
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DOI：
10.2174/15701786113109990046
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发表时间：
2013-12-01
影响因子：
0.8
通讯作者：
Duan, Jin-Ao
中科院分区：
文献类型：
--
作者：
Shen, Min-Zhe;Shi, Zhi-Hao;Duan, Jin-Ao
灯盏乙素（1）在临床治疗脑梗塞、冠心病、心绞痛等方面有显著疗效。灯盏乙素（1）在体内易于转化，因此，构建其代谢产物的合成方法将在不久的将来非常重要。本工作首次建立了灯盏乙素体内代谢产物6-O-甲基灯盏乙素（3）的高效合成方法。首先用二苯醚中的二氯二苯基甲烷保护灯盏乙素中C-6和C-7的二羟基（2）。然后，用苄基溴选择性地保护10中C-4 ′和C-7位的羟基。经七步反应，以高产率得到6-O-甲基黄芩素（3）。
Scutellarin (1) possesses distinguished efficacy in the clinical therapy of cerebral infarction, coronary heart disease, and angina pectoris. Scutellarin (1) is readily converted in vivo, therefore, synthetic methods for the construction of its metabolites will be very important in the near future. In this work, an efficient and first synthetic method for 6-O-methyl-scutellarein (3), one metabolite of scutellarin in vivo, is developed. Dichlorodiphenylmethane in diphenyl ether is used firstly to protect the dihydroxy groups at C-6 and C-7 in scutellarein (2). Then, benzyl bromide is used to selectively protect the hydroxy groups at C-4' and C-7 in 10. 6-O-Methyl-scutellarein (3) is obtained in high yield through seven steps.