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Synthese von Makroheterocyclen durch intramolekulare oxidative Kupplung von furanoiden β-Ketoestern

Authors

  • Prof. Dr. K. C. Nicolaou,

    Corresponding author
    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
    • Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Christopher R. H. Hale,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Christian Ebner,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Dr. Christian Nilewski,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Christopher F. Ahles,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Derek Rhoades

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Diese Arbeit wurde durch die National Institutes of Health (grant AI055475-10) und das Skaggs Institute of Research finanziell unterstützt. C.R.H.H. dankt für ein NSF Graduate Research Fellowship, C.E. für ein Otto Bayer-Stipendium der Bayer Science & Education Foundation und C.N. für ein Feodor Lynen-Forschungsstipendium der Alexander von Humboldt-Stiftung. Wir danken Dr. R. K. Chadha für die Kristallstrukturanalyse.

Abstract

original image

Cerammoniumnitrat (CAN) ermöglicht die oxidative radikalische Cyclisierung von furanoiden β-Ketoestern zu Makrocyclen verschiedener Ringgrößen. Die Reaktion toleriert Olefine und Alkine, Oxygenierung sowie Stickstoff- und Sauerstoffheterocyclen.

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