title: Catalytic enantioselective synthesis of functionalized tropanes reveals novel inhibitors of hedgehog signaling.
abstract: Dipolar cycloaddition: A highly efficient copper(I)-catalyzed enantioselective [3+2] cycloaddition reaction of 1,3-fused cyclic azomethine ylides and nitroalkenes has been developed. This method provides access to functionalized tropane scaffolds with several quaternary and tertiary stereocenters in a single step under mild reaction conditions.
authors.affiliation: Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany).
authors.forename: Rishikesh
authors.initials: R
authors.lastname: Narayan
authors.forename: Jonathan O
authors.initials: JO
authors.lastname: Bauer
authors.forename: Carsten
authors.initials: C
authors.lastname: Strohmann
authors.forename: Andrey P
authors.initials: AP
authors.lastname: Antonchick
authors.forename: Herbert
authors.initials: H
authors.lastname: Waldmann
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D053823:Hedgehog Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D015398:Signal Transduction; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D053823:Hedgehog Proteins; D014326:Tropanes
keywords: asymmetric catalysis; cycloaddition; hedgehog pathway; nitroalkenes; tropanes