Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Development of a β-C–H Bromination Approach toward the Synthesis of Jerantinine E
Christa K. G. Gerlinger, Tatjana Huber, Thomas Magauer, Teresa A. Preuhs
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01095

DOI: 10.1021/acs.joc.7b01095

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