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

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2017

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Huber, Tatjana
Preuhs, Teresa A.
Magauer, Thomas

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The Journal of Organic Chemistry. 2017, 82(14), pp. 7410-7419. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.7b01095

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.

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540 Chemie

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ISO 690HUBER, Tatjana, Teresa A. PREUHS, Christa K. G. GERLINGER, Thomas MAGAUER, 2017. Development of a β-C–H Bromination Approach toward the Synthesis of Jerantinine E. In: The Journal of Organic Chemistry. 2017, 82(14), pp. 7410-7419. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.7b01095
BibTex
@article{Huber2017Devel-40514,
  year={2017},
  doi={10.1021/acs.joc.7b01095},
  title={Development of a β-C–H Bromination Approach toward the Synthesis of Jerantinine E},
  number={14},
  volume={82},
  issn={0022-3263},
  journal={The Journal of Organic Chemistry},
  pages={7410--7419},
  author={Huber, Tatjana and Preuhs, Teresa A. and Gerlinger, Christa K. G. and Magauer, Thomas}
}
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