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Development of a β-C-H Bromination Approach toward the Synthesis of Jerantinine E.

Tatjana HuberTeresa A PreuhsChrista K G GerlingerThomas Magauer
Published in: The Journal of organic chemistry (2017)
The development of an asymmetric and highly convergent three-component synthesis of the functionalized ABC ring system of the Aspidosperma alkaloid jerantinine E is reported. The presented synthetic strategy relies on our recently developed method for the one-pot β-C-H bromination of enones, which allows for rapid construction of the tricyclic tetrahydrocarbazolone core via a palladium-catalyzed amination and oxidative indole formation. Moreover, a secondary amine building block that contains all carbon atoms of the D and E ring of the natural product could be installed in three additional steps.
Keyphrases
  • mass spectrometry
  • liquid chromatography