The Journal of organic chemistry

Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues

AB Smith, JB Sperry, Q Han

Index: Smith III, Amos B.; Sperry, Jeffrey B.; Han, Qiang Journal of Organic Chemistry, 2007 , vol. 72, # 18 p. 6891 - 6900

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Citation Number: 42

Abstract

Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components,(-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first-and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein ...