4.8 Article

Concise Total Syntheses of Aspalathin and Nothofagin

Journal

ORGANIC LETTERS
Volume 12, Issue 7, Pages 1580-1583

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol100315g

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Funding

  1. National Institutes of Health [SC2 GM081064-01]
  2. ACS Petroleum Research Fund [PRF45277-B1]
  3. Henry Dreyfus Teacher-Scholar Award

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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)phenyl acetylene. 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.

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