Totalsynthese des Vancomycin-Aglycons – Teil 2: Synthese der Aminosäuren 1–3 und Aufbau des AB-COD-DOE-Ringgerüsts

Authors

  • K. C. Nicolaou,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Nareshkumar F. Jain,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Swaminathan Natarajan,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Robert Hughes,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Michael E. Solomon,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Hui Li,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Joshi M. Ramanjulu,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Masaru Takayanagi,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Alexandros E. Koumbis,

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author
  • Toshikazu Bando

    1. Department of Chemistry und, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-2469 (und) Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
    Search for more papers by this author

Abstract

Eine Triazeneinheit als Schlüsselstruktur für die Synthese komplexer Biarylether und eine Suzuki-Kupplung waren die wesentlichen Merkmale beim Aufbau der Vorstufe 1 des Aglycons von Vancomycin, die bereits das vollständige Grundgerüst der Zielverbindung enthält; dabei wurde die Triazen-Methode im Zuge dieser Synthese entwickelt. Die Abspaltung der Triazeneinheit vom D-Ring und die Entfernung der übrigen Schutzgruppen führten dann zum Aglycon von Vancomycin. Diese Strategie sollte sich auch erfolgreich für die Synthese anderer natürlich vorkommender Glycopetid-Antibiotika einsetzen lassen und bietet Möglichkeiten für den Aufbau kombinatorischer Bibliotheken von Verbindungen der Vancomycin-Familie für biologische Studien.

Ancillary