Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 50, Pages 12149-12152Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201702648
Keywords
alkaloids; C-H activation; cobalt(III); isoquinolones; pyridones
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Funding
- Alfried Krupp von Bohlen und Halbach Foundation
- Deutsche Forschungsgemeinschaft
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Herein, we report a Cp*Co-III-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.
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