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

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

doi:10.1021/acs.joc.7b01095

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

J Org Chem. 2017 Jul 21;82(14):7410-7419. doi: 10.1021/acs.joc.7b01095. Epub 2017 Jun 28.

Authors

Tatjana Huber¹, Teresa A Preuhs¹, Christa K G Gerlinger², Thomas Magauer^{1

3}

Affiliations

¹ Department of Chemistry and Pharmacy, Ludwig-Maximilians-University , 81377 Munich, Germany.
² Faculty of Chemistry, University of Konstanz , 78457 Konstanz, Germany.
³ Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck , 6020 Innsbruck, Austria.

PMID: 28621133
DOI: 10.1021/acs.joc.7b01095

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Halogenation
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Models, Molecular
Molecular Structure

Substances

Indole Alkaloids
jerantinine E