Lerchen Andreas, Knecht Tobias, Koy Maximilian, Daniliuc Constantin G, Glorius Frank
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
Chemistry. 2017 Sep 7;23(50):12149-12152. doi: 10.1002/chem.201702648. Epub 2017 Jul 11.
Herein, we report a Cp*Co -catalyzed C-H activation approach as the key step to create highly valuable isoquinolones and pyridones as building blocks that can readily be applied in the total syntheses of a variety of aromathecin, protoberberine, and tylophora alkaloids. This particular C-H activation/annulation reaction was achieved with several terminal as well as internal alkyne coupling partners delivering a broad scope with excellent functional group tolerance. The synthetic applicability of this protocol reported herein was demonstrated in the total syntheses of two Topo-I-Inhibitors and two 8-oxyprotoberberine cores that can be further elaborated into the tetrahydroprotoberberine and the protoberberine alkaloid core. Moreover these building blocks were also transformed to six different tylophora alkaloids in expedient fashion.
在此，我们报道了一种Cp*Co催化的C-H活化方法，作为创建高价值异喹啉酮和吡啶酮作为构建模块的关键步骤，这些构建模块可轻松应用于多种芳香霉素、原小檗碱和娃儿藤生物碱的全合成。这种特定的C-H活化/环化反应通过几种末端和内炔偶联伙伴得以实现，具有广泛的底物范围和出色的官能团耐受性。本文报道的该方案的合成适用性在两种拓扑异构酶I抑制剂和两个8-氧代原小檗碱核心的全合成中得到了证明，这些核心可进一步转化为四氢原小檗碱和原小檗碱生物碱核心。此外，这些构建模块还以简便的方式转化为六种不同的娃儿藤生物碱。
