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Total Synthesis and Biological Evaluation of Jerantinine E

Authors

  • Dr. Reto Frei,

    1. Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
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  • Davide Staedler,

    1. Laboratory of Synthesis and Natural Products, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LSPN, BCH 5302, 1015 Lausanne (Switzerland)
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  • Aruna Raja,

    1. Department of Chemical Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • Dr. Raimo Franke,

    1. Department of Chemical Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • Dr. Florenz Sasse,

    1. Department of Chemical Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • Dr. Sandrine Gerber-Lemaire,

    1. Laboratory of Synthesis and Natural Products, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LSPN, BCH 5302, 1015 Lausanne (Switzerland)
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  • Prof. Dr. Jérôme Waser

    Corresponding author
    1. Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
    • Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/===

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  • We thank F. Hoffmann-La Roche Ltd for an unrestricted research grant and the Swiss State Secretariat for Education, Research and Innovation for financial support (Grant number C10.0116 in framework of the COST action CM0804). We thank Dr. Filippo De Simone (LCSO) for the first synthesis of Weinreb amide 8 and helpful discussions, as well as Prof. T. S. Kam from the University of Malaya for a copy of the original NMR spectra of Jerantinine E (5).

Abstract

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Natürliche Schönheit: Die erste Totalsynthese des Alkaloids Jerantinin E beruht auf der selektiven Cyclisierung eines Aminocyclopropans. Erste Studien zeigen, dass der Naturstoff die Tubulinpolymerisation hemmt und signifikant zytotoxisch und antimigratorisch auf Brustkrebs- und Lungenkrebs-Zelllinien wirkt.

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