Formal total syntheses of (+)-prelaureatin and (+)-laurallene by diastereoselective brook rearrangement-mediated [3 + 4] annulation.
Formal total syntheses of (+)-prelaureatin and (+)-laurallene by diastereoselective brook rearrangement-mediated [3 + 4] annulation.
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DOI：
10.1021/jo100708n
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发表时间：
2010-05
期刊：
影响因子：
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通讯作者：
M. Sasaki;Kazuhisa Oyamada;K. Takeda
中科院分区：
文献类型：
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作者：
M. Sasaki;Kazuhisa Oyamada;K. Takeda
本文叙述了卤代八元环醚（+）-前月桂精（1）和（+）-月桂烯（2）的形式合成。我们的策略的关键步骤依赖于通过用丙烯酰基硅烷9和6-氧杂-2-环庚烯酮衍生物22 '的Brook重排介导的[3 + 4]环化非对映选择性构建反式-α，α'-二取代的氧茂结构。
The formal syntheses of (+)-prelaureatin (1) and (+)-laurallene (2), halogenated eight-membered-ring ethers, are described. The key step of our strategy relies on diastereoselective construction of a trans-alpha,alpha'-disubstituted oxocene structure through a Brook rearrangement-mediated [3 + 4] annulation with acryloylsilane 9 and 6-oxa-2-cycloheptenone derivative 22'.