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  The Organocatalytic Approach to Enantiopure 2H- and 3H- Pyrroles: Inhibitors of the Hedgehog Signaling Pathway

Kötzner, L., Leutzsch, M., Sievers, S., Patil, S., Waldmann, H., Zheng, Y., et al. (2016). The Organocatalytic Approach to Enantiopure 2H- and 3H- Pyrroles: Inhibitors of the Hedgehog Signaling Pathway. Angewandte Chemie International Edition, 55(27), 7693-7697. doi:10.1002/anie.201602932.

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anie201602932-sup-0001-misc_information.pdf (Supplementary material), 4MB
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 Creators:
Kötzner, Lisa1, Author              
Leutzsch, Markus1, Author              
Sievers, Sonja2, Author
Patil, Sumersing3, Author
Waldmann, Herbert3, Author
Zheng, Yiying4, Author              
Thiel, Walter4, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Max-Planck-Institut für Molekulare Physiologie, Compound Management and Screening Center (COMAS), Dortmund, Germany, ou_persistent22              
3Max-Planck-Institut für Molekulare Physiologie, Dortmund, Germany Germany, ou_persistent22              
4Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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Free keywords: [1,5]-alkyl shifts; 2H-pyrroles; 3H-pyrroles; Brønsted acid catalysis; Hedgehog signaling inhibitors
 Abstract: A divergent approach to enantioenriched 2H- and 3H-pyrroles catalyzed by a spirocyclic phosphoric acid is reported that makes use of a Fischer-type indolization and a [1,5]-alkyl shift. Catalyzed by the chiral phosphoric acid STRIP, good to excellent yields and enantioselectivities could be obtained. Remarkably, biological evaluation reveals one of these novel 2H-pyrroles to be a potent but nontoxic inhibitor of the Hedgehog signaling pathway by binding to the Smoothened protein.

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Language(s): eng - English
 Dates: 2016-03-242016-05-302016-06-27
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201602932
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 55 (27) Sequence Number: - Start / End Page: 7693 - 7697 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851