Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 14, Pages 7410-7419Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01095
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Funding
- Funds of the Chemical Industry (Sachkostenzuschuss and Dozentenpreis)
- German Research Foundation [SFB 749, SFB TRR 152]
- German National Academic Foundation
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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.
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