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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

original image

Eine stereoselektive Tandemsequenz bestehend aus Cyclisierung, 1,5-Wanderung und intermolekularer Cyclopropanierung ermöglichte die erste Totalsynthese des antiviralen Naturstoffs (+)-Schisanwilsonen A. Die Schlüsselsequenz wird durch einen Goldkomplex katalysiert.

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