Erythribyssin H类似物的设计与合成
Design and Synthesis of the Derivative of Erythribyssin H

作者: 王亚楼 , 唐文婧 , 巫 凯 :中国药科大学药物化学教研室,南京;

关键词: 2-(4-羟基-35-二甲氧基苯基)-6-羟基苯并呋喃Erythribyssin H类似物Vilsmier-Schmidet反应交叉McMurry偶联反应合成 2-(4-Hydroxy-35-dimethoxyphenyl)-6-hydroxybenzofuran Erythribyssin H Derivative Vilsmier-Schmidet Reaction Cross Mcmurry Coupling Reaction Synthesis


目的:提供合成Erythribyssin H类似物(2)的路线。方法:以间苯二酚和丁香醛为起始原料,经Vilsmier- schmidet反应和酚羟基保护反应合成2-羟基4-苄氧基苯甲醛(4)3,5-二甲氧基4-苄氧基苯甲醛(5)。然后使用McMurry交叉偶联反应得到邻乙烯基苯酚产物(6)6I2/K2CO3试剂作用下环合并脱保护成为Erythribyssin H类似物(2)。结果:目标化合物和相应的中间体的化学结构都经过1H-NMRIRMS确证。结论:以间苯二酚和丁香醛为起始原料经McMurry交叉偶联反应合成了Erythribyssin H类似物(2),该合成路线简单,易于操作,(2)的总收率为31%

Objective: To develop a synthetic route for Erythribyssin H derivative. Methods: 2-(4-Hydroxy-3, 5-dimethoxyphenyl)-6-hydroxybenzofuran (Erythribyssin H derivative, compound 2) can be synthesized from resorcinol and syringaldehyde by Vilsmier-schmidet reaction to get two key intermediates 4-benzyloxyl-2-hydroxybenzaldehyde (compound 4) and 3,5-dimethoxy-4-benzyloxyl- benzaldehyde (compound 5). Then via McMurry coupling reaction the two intermediate products developed to be cross coupling product 5-(benzyloxy)-2-(4-(benzyloxy)-3,5-dimethox-ysty-ryl)- phenol (compound 6). The product went through oxidative cyclization reaction, deprotective reaction, finally developed to be the derivative of Erythribyssin H(2). Results: The structure of all products was confirmed by 1H-NMR, IR and MS analysis. Conclusion: Erythribyssin H derivative was synthesized from resorcinol and syringaldehyde via McMurry coupling reaction, which is easy to conduct, and the overall yield is 31%.

文章引用: 王亚楼 , 唐文婧 , 巫 凯 (2014) Erythribyssin H类似物的设计与合成。 药物化学, 2, 14-19. doi: 10.12677/HJMCe.2014.22003


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