z-logo
Premium
The Organocatalytic Approach to Enantiopure 2 H ‐ and 3 H ‐Pyrroles: Inhibitors of the Hedgehog Signaling Pathway
Author(s) -
Kötzner Lisa,
Leutzsch Markus,
Sievers Sonja,
Patil Sumersing,
Waldmann Herbert,
Zheng Yiying,
Thiel Walter,
List Benjamin
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602932
Subject(s) - enantiopure drug , hedgehog signaling pathway , hedgehog , chemistry , stereochemistry , signal transduction , biochemistry , catalysis , enantioselective synthesis
Abstract A divergent approach to enantioenriched 2 H ‐ and 3 H ‐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 2 H ‐pyrroles to be a potent but nontoxic inhibitor of the Hedgehog signaling pathway by binding to the Smoothened protein.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here