Abstract
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.
Keywords: 6-O-methyl-scutellarein, metabolite, scutellarin, synthesis, regioselective protection.
Letters in Organic Chemistry
Title:Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation
Volume: 10 Issue: 10
Author(s): Min-Zhe Shen, Zhi-Hao Shi, Nian-Guang Li, Hao -Tang, Qian-Ping Shi, Yu-Ping Tang, Jian-Ping Yang and Jin-Ao Duan
Affiliation:
Keywords: 6-O-methyl-scutellarein, metabolite, scutellarin, synthesis, regioselective protection.
Abstract: 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.
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Cite this article as:
Shen Min-Zhe, Shi Zhi-Hao, Li Nian-Guang, -Tang Hao, Shi Qian-Ping, Tang Yu-Ping, Yang Jian-Ping and Duan Jin-Ao, Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation, Letters in Organic Chemistry 2013; 10 (10) . https://dx.doi.org/10.2174/15701786113109990046
DOI https://dx.doi.org/10.2174/15701786113109990046 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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