Synthesis and assignment of absolute configuration of (-)-oleocanthal: a potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils.
[structure: see text] Effective total syntheses and the assignment of absolute configurations of both the (+)- and (-)-enantiomers of oleocanthal 1 (a.k.a. deacetoxy ligstroside aglycon), the latter derived from extra virgin olive oils and known to be responsible for the back of the throat irritant properties of olive oils, have been achieved. The absolute and relative stereochemistry of the naturally occurring enantiomer (-)-1 proved to be 3S,4E. Both syntheses begin with d-(-)-ribose, proceed in 12 steps, and are achieved with an overall yield of 7%. Both enantiomers proved to be non-steroidal anti-inflammatory and anti-oxidant agents.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, 19104, USA. smithab@sas.upenn.edu
Han
Qiang
Q
Breslin
Paul A S
PA
Beauchamp
Gary K
GK
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D000081004:Cyclopentane Monoterpenes; D015394:Molecular Structure; D000069463:Olive Oil; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D000081004:Cyclopentane Monoterpenes; D000069463:Olive Oil; D010636:Phenols; D010938:Plant Oils; C503534:oleocanthal