NHC 催化偕烯醇与喹唑酮的分子内环化反应立体选择性构建去氧十字孢碱类生物碱。
Stereoselective construction of deoxy-cruciferane alkaloids by NHC-catalyzed intramolecular annulation of homoenolate with quinazolinone.
机构信息
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India and Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Pune 411008, India.
出版信息
Org Biomol Chem. 2019 Aug 14;17(30):7135-7139. doi: 10.1039/c9ob01243e. Epub 2019 Jul 19.
Chiral N-heterocyclic carbene (NHC)-catalyzed intramolecular [3 + 2] annulation of enals with an unactivated imine moiety of quinazolinone via formal homoenolate cycloaddition has been demonstrated. It is an excellent approach for stereoselective syntheses of deoxy-cruciferane alkaloids comprising a biologically important pyrroloindoline scaffold. Notably, this is the first report on the NHC-catalyzed asymmetric intramolecular homoenolate annulation with cyclic N-acyl amidine.
手性 N-杂环卡宾（NHC）催化的通过形式偕胺肟环加成的烯醛与喹唑啉酮中未活化的亚胺部分的分子内[3 + 2]环加成已经得到证明。这是通过立体选择性合成包含生物重要吡咯并吲哚骨架的脱氧 Cruciferane 生物碱的极好方法。值得注意的是，这是首例关于 NHC 催化的具有环状 N-酰基脒的不对称分子内偕胺肟环加成的报道。
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