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Total Synthesis of Carolacton, a Highly Potent Biofilm Inhibitor

Authors

  • Thomas Schmidt,

    1. Institut für Organische Chemie und Zntrum für Biomolekulare Wirkstoffe (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany)
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  • Prof. Dr. Andreas Kirschning

    Corresponding author
    1. Institut für Organische Chemie und Zntrum für Biomolekulare Wirkstoffe (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany)
    • Institut für Organische Chemie und Zntrum für Biomolekulare Wirkstoffe (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany)
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  • We are indepted to R. Jansen and R. Müller (Helmholtz-Zentrum für Infektionsforschung, HZI, Braunschweig (Germany)) for an authentic sample of carolacton (1) and thank the referees for helpful suggestions.

Abstract

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Metals are the key players in the synthesis of caralacton, a strong inhibitor of bacterial biofilms. The total synthesis is based on several metal-mediated key transformations such as the Ley and the Duthaler–Hafner aldol reactions, the Marshall reaction and Breit's substitution, as well as the Nozaki–Hiyama–Kishi and Negishi–Fu C[BOND]C coupling reactions.

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