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

Kötzner, Lisa; Leutzsch, Markus; Sievers, Sonja; Patil, Sumersing; Waldmann, Herbert; Zheng, Yiying; Thiel, Walter; List, Benjamin

doi:10.1002/anie.201602932

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

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Kötzner, Lisa
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch, Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zheng, Yiying
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel, Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002A-4EBC-9

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.