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Huber, Tatjana; Preuhs, Teresa A.; Gerlinger, Christa K. G.; Magauer, Thomas (2017): Development of a beta-C-H Bromination Approach toward the Synthesis of Jerantinine E. In: Journal of Organic Chemistry, Vol. 82, No. 14: pp. 7410-7419
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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 beta-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.