Catalytic Enantioselective Synthesis of Functionalized Tropanes Reveals Novel Inhibitors of Hedgehog Signaling†
Dr. Rishikesh Narayan
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Search for more papers by this authorJonathan O. Bauer
Technische Universität Dortmund, Fakultät Chemie und Chemische Biologie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorProf. Dr. Carsten Strohmann
Technische Universität Dortmund, Fakultät Chemie und Chemische Biologie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorCorresponding Author
Dr. Andrey P. Antonchick
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät für Chemie und Chemische Biologie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)===Search for more papers by this authorCorresponding Author
Prof. Dr. Herbert Waldmann
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät für Chemie und Chemische Biologie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)===Search for more papers by this authorDr. Rishikesh Narayan
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Search for more papers by this authorJonathan O. Bauer
Technische Universität Dortmund, Fakultät Chemie und Chemische Biologie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorProf. Dr. Carsten Strohmann
Technische Universität Dortmund, Fakultät Chemie und Chemische Biologie, Anorganische Chemie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Search for more papers by this authorCorresponding Author
Dr. Andrey P. Antonchick
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät für Chemie und Chemische Biologie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)===Search for more papers by this authorCorresponding Author
Prof. Dr. Herbert Waldmann
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
Technische Universität Dortmund, Fakultät für Chemie und Chemische Biologie, Chemische Biologie, Otto-Hahn-Strasse 6, 44221 Dortmund (Germany)
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)===Search for more papers by this authorWe acknowledge funding from the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013; ERC Grant 268309). J.O.B. thanks the Fonds der Chemischen Industrie for a fellowship.
Graphical 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.
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