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Synthesis of Cyclopamine Using a Biomimetic and Diastereoselective Approach

Authors

  • Athanassios Giannis Prof. Dr.,

    1. Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103 Leipzig (Germany), Fax: (+49) 341-973-6599
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  • Philipp Heretsch Dipl.-Chem.,

    1. Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103 Leipzig (Germany), Fax: (+49) 341-973-6599
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  • Vasiliki Sarli Dr.,

    1. Laboratory of Organic Chemistry, Department of Chemistry, University of Thessaloniki, 54124 Thessaloniki (Greece)
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  • Anne Stößel Dipl.-Chem.

    1. Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, 04103 Leipzig (Germany), Fax: (+49) 341-973-6599
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  • We thank Dr. Lothar Hennig for recording NMR spectra and for his help in interpreting the 2D NMR spectra. The Deutsche Forschungsgemeinschaft (DFG) is acknowledged for partial financial support. P.H. is a fellow of Fonds der Chemischen Industrie.

Abstract

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From Homer to hedgehog: Cyclopamine, the first inhibitor of the hedgehog signaling pathway, causes cyclopia in embryos but in adults it is a potent anticancer drug. A concise biomimetic and diastereoselective synthesis of cyclopamine (2) starting from commercially available dehydroepiandrosterone (1) now also provides access to several analogues.

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