The First Synthesis of Uralenol, 5′-Prenylated Quercetin, via Palladium-Catalyzed O-Dimethylallylation Reaction with Concurrent Acetyl Migration
The First Synthesis of Uralenol, 5′-Prenylated Quercetin, via Palladium-Catalyzed O-Dimethylallylation Reaction with Concurrent Acetyl Migration
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DOI：
10.1055/s-0033-1338559
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发表时间：
2014-01-01
影响因子：
2.6
通讯作者：
Nemoto, Hisao
中科院分区：
文献类型：
--
作者：
Kawamura, Tomoyuki;Hayashi, Moemi;Nemoto, Hisao
首次报道了5 ′-异戊二烯化槲皮素--乌拉烯醇的合成。关键步骤是钯催化的O-1，1-二甲基烯丙基化反应，同时乙酰基迁移，得到所需的中间体作为主要异构体，其通过重结晶纯化。最后，Claisen重排，然后脱保护的所有酚保护基，以优异的产率提供乌拉烯醇。
The first synthesis of uralenol, 5'-prenylated quercetin, is described. The key step is a palladium-catalyzed O-1,1-dimethylallylation reaction, with concurrent acetyl migration to afford the desired intermediate as a major isomer, which was purified by recrystallization. Finally, Claisen rearrangement, followed by de-protection of all phenolic protecting groups, afforded uralenol in excellent yield.