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

作者：Huber Tatjana; Preuhs Teresa A; Gerlinger Christa K G; Magauer Thomas

来源：Journal of Organic Chemistry, 2017, 82(14): 7410-7419.

DOI：10.1021/acs.joc.7b01095

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.

• 出版日期2017-7-21