{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,26]],"date-time":"2026-10-26T17:30:36Z","timestamp":1793035836323,"version":"4.5.0"},"reference-count":19,"publisher":"Informa UK Limited","issue":"12","license":[{"start":{"date-parts":[[2015,12,2]],"date-time":"2015-12-02T00:00:00Z","timestamp":1449014400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"funder":[{"name":"grant-aid for scientific research","award":["no. 26450143"],"award-info":[{"award-number":["no. 26450143"]}]}],"content-domain":{"domain":["www.tandfonline.com"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[2015,12,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>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.<\/jats:p>","DOI":"10.1080\/09168451.2015.1058704","type":"journal-article","created":{"date-parts":[[2015,6,18]],"date-time":"2015-06-18T15:30:21Z","timestamp":1434641421000},"page":"1926-1930","update-policy":"https:\/\/doi.org\/10.1080\/tandf_crossmark_01","source":"Crossref","is-referenced-by-count":15,"title":["New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step"],"prefix":"10.1080","volume":"79","author":[{"given":"Kazuki","family":"Yashiro","sequence":"first","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmaceutical Science, Keio University , Tokyo, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kengo","family":"Hanaya","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmaceutical Science, Keio University , Tokyo, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mitsuru","family":"Shoji","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmaceutical Science, Keio University , Tokyo, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takeshi","family":"Sugai","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmaceutical Science, Keio University , Tokyo, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"301","published-online":{"date-parts":[[2015,12,2]]},"reference":[{"key":"2021033107580985900_CIT0001","doi-asserted-by":"publisher","first-page":"945","DOI":"10.1271\/bbb.58.945","article-title":"Isolation and identification of antimicrobial compounds in Brazilian propolis","volume":"58","author":"Aga","year":"1994","journal-title":"Biosci. 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