869477-01-0

Upstream product

• 116669-78-4 (4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 869476-97-1 (3aS,6aS)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 869477-00-9 [(3aR,4E,5R,6aS)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 369647-26-7 (4R,5S)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-propen-1-ol 

Relevant academic research and scientific papers

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

(Chemical Equation Presented) 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.

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

(Chemical Equation Presented) 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.