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Concise Total Syntheses of Aspalathin and Nothofagin

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journal contribution
posted on 02.04.2010, 00:00 by Akop Yepremyan, Baback Salehani, Thomas G. Minehan
Syntheses of the C-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.