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Concise Total Syntheses of Aspalathin and Nothofagin

Akop Yepremyan, Baback Salehani, Thomas G Minehan

Org Lett. 2010 Apr 2;12(7):1580-3.

PMID: 20222686

Abstract:

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 beta-C-aryl glycoside in 30-65% yields.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
LS7931201 2,4-bis(benzyloxy)pyrimidine-5-boronic acid 2,4-bis(benzyloxy)pyrimidine-5-boronic acid Price
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