Diastereoselective brook rearrangement-mediated [3+4] annulation: Application to a formal synthesis of (+)-laurallene
Diastereoselective brook rearrangement-mediated [3+4] annulation: Application to a formal synthesis of (+)-laurallene
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DOI：
10.1021/ol8003595
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发表时间：
2008-05-01
期刊：
影响因子：
5.2
通讯作者：
Takeda, Kei
中科院分区：
文献类型：
--
作者：
Sasaki, Michiko;Hashimoto, Azusa;Takeda, Kei
卤代八元环醚(+)-月桂烯的正式合成已完成。该合成涉及使用丙烯酰硅烷 10 和 6-oxa-2-环庚烯酮 9 通过 Brook 重排介导的 [3 + 4] 环化构建反式 α,α'-二取代氧新烯结构 16，并将其转化为 2，后者已被 Crimmins 和同事转化为 (+)-月桂烯。
The formal synthesis of (+)-laurallene, a halogenated eight-membered ring ether, was accomplished. The synthesis involves construction of a trans alpha,alpha'-disubstituted oxocene structure 16 through a Brook rearrangement-mediated [3 + 4] annulation using acryloylsilane 10 and 6-oxa-2-cycloheptenone 9 and its conversion into 2, which has been transformed into (+)-laurallene by Crimmins and co-workers.