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

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 a...

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Veröffentlicht in:Journal of organic chemistry 2017-07, Vol.82 (14), p.7410-7419
Hauptverfasser: Huber, Tatjana, Preuhs, Teresa A, Gerlinger, Christa K. G, Magauer, Thomas
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01095