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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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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crinformauk:10.1080/09168451.2015.1058704 2024-09-15T17:48:19+00:00 New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step Yashiro, Kazuki Hanaya, Kengo Shoji, Mitsuru Sugai, Takeshi grant-aid for scientific research 2015 http://dx.doi.org/10.1080/09168451.2015.1058704 http://academic.oup.com/bbb/article-pdf/79/12/1926/36820704/bbb1926.pdf en eng Informa UK Limited https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model Bioscience, Biotechnology, and Biochemistry volume 79, issue 12, page 1926-1930 ISSN 0916-8451 1347-6947 journal-article 2015 crinformauk https://doi.org/10.1080/09168451.2015.1058704 2024-08-05T04:23:03Z 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. Article in Journal/Newspaper Antarc* Antarctica Informa Bioscience, Biotechnology, and Biochemistry 79 12 1926 1930 |
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English |
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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. |
author2 |
grant-aid for scientific research |
format |
Article in Journal/Newspaper |
author |
Yashiro, Kazuki Hanaya, Kengo Shoji, Mitsuru Sugai, Takeshi |
spellingShingle |
Yashiro, Kazuki Hanaya, Kengo Shoji, Mitsuru Sugai, Takeshi New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
author_facet |
Yashiro, Kazuki Hanaya, Kengo Shoji, Mitsuru Sugai, Takeshi |
author_sort |
Yashiro, Kazuki |
title |
New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
title_short |
New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
title_full |
New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
title_fullStr |
New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
title_full_unstemmed |
New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
title_sort |
new synthesis of artepillin c, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step |
publisher |
Informa UK Limited |
publishDate |
2015 |
url |
http://dx.doi.org/10.1080/09168451.2015.1058704 http://academic.oup.com/bbb/article-pdf/79/12/1926/36820704/bbb1926.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Bioscience, Biotechnology, and Biochemistry volume 79, issue 12, page 1926-1930 ISSN 0916-8451 1347-6947 |
op_rights |
https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model |
op_doi |
https://doi.org/10.1080/09168451.2015.1058704 |
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Bioscience, Biotechnology, and Biochemistry |
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79 |
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12 |
container_start_page |
1926 |
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1930 |
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1810289463526424576 |