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A three-component coupling approach to the ACE-ring substructure of C19-diterpene alkaloids.
The Journal of Antibiotics ( IF 3.3 ) Pub Date : 2018-Feb-01 , DOI: 10.1038/ja.2017.69
Kosuke Minagawa , Daisuke Urabe , Masayuki Inoue

C19-diterpene alkaloids are a class of alkaloids with pharmacologically important activities having an intricately fused hexacyclic ABCDEF-ring system. Here we report expeditious assembly of the ACE-ring substructure 4a by applying a three-component coupling strategy. A radical-polar crossover reaction between an AE-ring radical precursor, a C-ring radical acceptor and an aldehyde was realized by the actions of Et3B and O2, resulting in the installation of three new stereocenters and extension of the carbon chain corresponding to the B-ring. As the ACE-ring 4a possesses the correct C4,11-quaternary and C10-tertiary carbons, 4a would serve as an advanced intermediate for constructing the entire C19-diterpene alkaloid structures.

中文翻译:

C19-二萜生物碱的ACE环亚结构的三组分偶联方法。

C19-二萜生物碱是一类具有药理学重要活性的生物碱,具有复杂稠合的六环ABCDEF-环系统。在这里,我们报告通过应用三组件耦合策略快速组装ACE环子结构4a。通过Et 3 B和O 2的作用,实现了AE环自由基前体,C环自由基受体和醛之间的自由基-极性交叉反应,从而安装了三个新的立体中心并延伸了碳链对应于B环。由于ACE环4a具有正确的C4,11-季碳和C10-叔碳,因此4a将用作构建整个C19-二萜生物碱结构的高级中间体。
更新日期:2017-07-29
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