New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step

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 subseque...

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Bibliographic Details
Published in:Bioscience, Biotechnology, and Biochemistry
Main Authors: Yashiro, Kazuki, Hanaya, Kengo, Shoji, Mitsuru, Sugai, Takeshi
Other Authors: grant-aid for scientific research
Format: Article in Journal/Newspaper
Language:English
Published: Informa UK Limited 2015
Subjects:
Organic Chemistry
Molecular Biology
Applied Microbiology and Biotechnology
General Medicine
Biochemistry
Analytical Chemistry
Biotechnology
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1080/09168451.2015.1058704
http://academic.oup.com/bbb/article-pdf/79/12/1926/36820704/bbb1926.pdf
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Summary: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.

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