The Plakotenins: Biomimetic Diels–Alder Reactions, Total Synthesis, Structural Investigations, and Chemical Biology

Authors

  • Dr. Emmanuel Bourcet,

    1. Institute of Organic Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-48581
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  • Larissa Kaufmann,

    1. Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Campus North, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany)
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  • Dr. Stephanie Arzt,

    1. Institute of Organic Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-48581
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  • Dr. Angela Bihlmeier,

    1. Institute of Physical Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 2, 76131 Karlsruhe (Germany)
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  • Prof. Dr. Wim Klopper,

    1. Institute of Physical Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 2, 76131 Karlsruhe (Germany)
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  • Dr. Ute Schepers,

    1. Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Campus North, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany)
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  • Prof. Dr. Stefan Bräse

    Corresponding author
    1. Institute of Organic Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-48581
    2. Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Campus North, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany)
    • Institute of Organic Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-48581
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Abstract

The total synthesis of plakotenin, a cytotoxic marine natural product, using a biomimetic Diels–Alder reaction is described in detail. Two approaches were used, whereby the Diels–Alder reaction occurs at different stages of the synthesis. Homo- and nor-plakotenin, related natural products, were also prepared, as well as iso-plakotenin, a diastereoisomer of plakotenin. The syntheses prove the relative and absolute stereochemistry of the latter. The chemical biology of the plakotenins was investigated on selected compounds.

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