An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis
An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis
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DOI：
10.1002/anie.201301849
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发表时间：
2013-01-01
影响因子：
16.6
通讯作者：
Snyder, Scott A.
中科院分区：
文献类型：
--
作者：
ElSohly, Adel M.;Wespe, Daniel A.;Snyder, Scott A.
将它们合并在一起：大多数为secounega生物碱类开发的合成需要很长的序列来创建它们的丁烯内酯桥联结构域。一种新的方法使用N-杂环卡宾(NHCS)和Lewis酸从适当的前体一步伪造整个结构域，表明芳醛衍生的高烯醇类化合物可以在分子内环境中作为亲核剂参与(见方案)。
Folding it all together: Most of the syntheses developed for the securinega alkaloid class require lengthy sequences to create their bridging butenolide domains. A novel approach uses N-heterocyclic carbenes (NHCs) and Lewis acids to forge the entire domain in a single step from appropriate precursors, showing that ynal-derived homoenolates can participate as nucleophiles in intramolecular settings (see scheme).