New Synthesis of Artepillin C, a Prenylated Phenol, Utilizing Lipase-catalyzed Regioselective Deacetylation as the Key Step
New Synthesis of Artepillin C, a Prenylated Phenol, Utilizing Lipase-catalyzed Regioselective Deacetylation as the Key Step
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以脂肪酶催化区域选择性脱乙酰化为关键步骤新合成异戊二烯化苯酚 Artepillin C
DOI：
10.1080/09168451.2015.1058704
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发表时间：
2015
期刊：
影响因子：
--
通讯作者：
T. Sugai
中科院分区：
文献类型：
--
作者：
K. Yashiro;K. Hanaya;M. Shoji;T. Sugai
我们从2,6-二烯丙基苯酚中合成了artepillin C，这是一种从巴西蜂胶中分离得到的具有抗氧化和抗肿瘤活性的二烯丙基化对羟基肉桂酸酯。烯烃交叉复分解将末端乙烯基替换为2,2-二甲基乙烯基，随后转化为2,6-二戊基-1,4-对苯二酚二乙酸酯。南极假丝酵母脂酶b催化2-丙醇区域的去乙酰化选择性地去除较少阻碍的乙酰基，得到2,6-二戊基-1,4-对苯二酚1-单乙酸酯。通过钯介导的丙烯酸甲酯烯基化反应，得到一个三碳侧链。酯的最终水解生成青蒿素C。
We have synthesized artepillin C, a diprenylatedp-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 antarcticalipase 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.