Concise total syntheses of aspalathin and nothofagin.
Concise total syntheses of aspalathin and nothofagin.
复制标题
aspalathin 和 nothofagin 的简明全合成。
DOI：
10.1021/ol100315g
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发表时间：
2010
期刊：
影响因子：
5.2
通讯作者：
Minehan,ThomasG
中科院分区：
文献类型：
--
作者：
Yepremyan,Akop;Salehani,Baback;Minehan,ThomasG
以三苄基葡萄糖醛、三苄基间苯三酚、4-苄氧基苯乙炔或3，4-双苄氧基苯乙炔为原料，经八步反应合成了C-糖基黄酮类天然产物Aspalathin和nothofagin。合成的关键步骤涉及高度立体选择性的刘易斯酸促进的1，2-二-O-酰基-3，4，6-三苄基葡萄糖与三苄基间苯三酚的偶联，其以30−65%的产率产生相应的β-C-芳基糖苷。
Syntheses of theC-glycosyl flavone natural products aspalathin and nothofagin have been accomplished in eight steps from tribenzyl glucal, tribenzylphloroglucinol, and either 4-(benzyloxy)phenylacetylene or 3,4-bis(benzyloxy)phenylacetylene. The key step of the syntheses involves a highly stereoselective Lewis acid promoted coupling of 1,2-di-O-acyl-3,4,6-tribenzylglucose with tribenzylphloroglucinol, which gives rise to the corresponding β-C-aryl glycoside in 30−65% yields.