artepillin-c has been researched along with mequinol* in 1 studies
1 other study(ies) available for artepillin-c and mequinol
| Article | Year |
|---|---|
New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step.
We have synthesized artepillin C, a diprenylated p-hydroxycinnamate originally isolated from Brazilian propolis and exhibiting antioxidant and antitumor activities, from 2,6-diallylphenol. Replacement of the terminal vinyl with 2,2-dimethylvinyl group by olefin cross-metathesis and subsequent transformation yielded 2,6-diprenyl-1,4-hydroquinone diacetate. Candida antarctica lipase B-catalyzed deacetylation in 2-propanol regioselectively removed the less hindered acetyl group to give 2,6-diprenyl-1,4-hydroquinone 1-monoacetate. After triflation of the liberated 4-hydroxy group, a three-carbon side chain was introduced by palladium-mediated alkenylation with methyl acrylate. Final hydrolysis of the esters furnished artepillin C. Topics: Acetylation; Anisoles; Biocatalysis; Chemistry Techniques, Synthetic; Fungal Proteins; Lipase; Phenol; Phenylpropionates; Prenylation; Stereoisomerism; Substrate Specificity | 2015 |