New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step. Issue 12 (2nd December 2015)

• Record Type: Journal Article
• Authors: Yashiro, Kazuki; Hanaya, Kengo; Shoji, Mitsuru; Sugai, Takeshi
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 79:Issue 12(2015)
• Page Start: 1926
• Page End: 1930
• Publication Date: 2015-12-02
• Subjects: artepillin C -- lipase -- regioselective transesterification -- prenylated phenol; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2015.1058704
• Languages: English
• ISSNs: 0916-8451

Abstract

Abstract: 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. Graphical abstract: : Artepillin C, a natural prenylated phenol, was synthesized by lipase-catalyzed regioselective deacetylation on the disubstituted hydroquinone diacetate as the key step.