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Synthesis of (+)-Schisanwilsonene A by Tandem Gold-Catalyzed Cyclization/1,5-Migration/Cyclopropanation

Authors

  • Morgane Gaydou,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Dr. Ricarda E. Miller,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Nicolas Delpont,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Dr. Julien Ceccon,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Prof. Antonio M. Echavarren

    Corresponding author
    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
    2. Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel⋅li Domingo s/n, 43007 Tarragona (Spain)
    • Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)

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  • We thank the MICINN (CTQ2010-16088/BQU), the European Research Council (Advanced Grant No. 321066), the AGAUR (2009 SGR 47), and the ICIQ Foundation for financial support. We also thank M. Raducan, and Dr. N. J. A. Martin for preliminary experiments and the ICIQ X-Ray diffraction unit for the X-ray diffraction structures.

Abstract

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Going (anti)viral: The first total synthesis of the antiviral (+)-schisanwilsonene A has been completed using a fully stereoselective tandem cyclization/1,5-migration/intermolecular cyclopropanation. The key reaction sequence is catalyzed by gold.

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