| 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, possessessimilar 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 closelyrelated (−)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies.To demonstrate the utility of the second-generation synthesis, multigram quantities of (−)-oleocanthalwere prepared in 10 steps (14% overall yield) from commercially available d-lyxose.
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