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

J Org Chem. 2007 Aug 31;72(18):6891-900. doi: 10.1021/jo071146k. Epub 2007 Aug 8.

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 aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Biological Products / chemistry*
  • Cerium / chemistry
  • Chlorides / chemistry
  • Cyclization
  • Cyclopentane Monoterpenes
  • Ethylenes / chemistry
  • Iridoids
  • Ketones / chemical synthesis
  • Ketones / chemistry
  • Molecular Structure
  • Olive Oil
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Plant Oils / chemistry*
  • Pyrans / chemistry*

Substances

  • Aldehydes
  • Anti-Inflammatory Agents, Non-Steroidal
  • Biological Products
  • Chlorides
  • Cyclopentane Monoterpenes
  • Ethylenes
  • Iridoids
  • Ketones
  • Olive Oil
  • Phenols
  • Plant Oils
  • Pyrans
  • oleuropein
  • Cerium
  • ethylene
  • oleocanthal