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Cascade Syntheses Routes to the Centrocountins

Authors

  • Vincent Eschenbrenner-Lux,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
    2. Technische Universität Dortmund, Fakultät Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund (Germany)
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  • Dr. Heiko Dückert,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
    2. Technische Universität Dortmund, Fakultät Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund (Germany)
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  • Dr. Vivek Khedkar,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
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  • Dipl.-Chem. Hanna Bruss,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
    2. Technische Universität Dortmund, Fakultät Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund (Germany)
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  • Prof. Dr. Herbert Waldmann,

    Corresponding author
    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
    2. Technische Universität Dortmund, Fakultät Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund (Germany)
    • Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
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  • Dr. Kamal Kumar

    Corresponding author
    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
    2. Technische Universität Dortmund, Fakultät Chemische Biologie, Otto-Hahn-Str. 6, 44227 Dortmund (Germany)
    • Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Str. 11, 44227 Dortmund (Germany)
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Abstract

Cascade and domino reactions that proceed through multiple steps in one pot and include multiple bond formations are promising methods for the rapid and efficient generation of complex molecular architectures, including the scaffolds of classes of complex natural product. We describe the development of various one-pot cascade reaction sequences to yield centrocountins, which are tetracyclic indole derivatives with the basic scaffold of numerous polycyclic alkaloids. The mechanistic investigation of a sequence employing readily available alkynes and 3-formylchromones as starting materials provided evidence that this one-pot synthesis proceeds through at least twelve consecutive transformations and includes at least nine different chemical reactions, making it the longest cascade reaction sequence known to date. We describe the scope and limitations of the cascade synthesis approaches and the development of an enantioselectively catalyzed centrocountin synthesis.

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