Get access

Total Synthesis of Linoxepin through a Palladium-Catalyzed Domino Reaction

Authors

  • Prof. Dr. Lutz F. Tietze,

    Corresponding author
    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
    • Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)

    Search for more papers by this author
  • Dipl.-Chem. Svenia-C. Duefert,

    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
    Search for more papers by this author
  • Dr. Jérôme Clerc,

    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
    Search for more papers by this author
  • Dr. Matthias Bischoff,

    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
    Search for more papers by this author
  • Dipl.-Chem. Christian Maaß,

    1. Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)
    Search for more papers by this author
  • Prof. Dr. Dietmar Stalke

    1. Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)
    Search for more papers by this author

  • We thank the German Research Foundation (DFG), the Land Niedersachsen, the Volkswagen Foundation, and the Fonds der Chemischen Industrie for financial support. Special thanks to S. L. Buchwald for providing a sample of the KenPhos ligand. S.-C.D. thanks the Konrad Adenauer Foundation for a doctoral fellowship. J.C. thanks the Alexander von Humboldt Foundation for a postdoctoral fellowship. C.M. thanks the Land Niedersachsen for providing a fellowship in the Catalysis for Sustainable Synthesis (CaSuS) Ph.D. program. The photograph in the graphical abstract was taken by Thomas Hundtke.

Abstract

original image

Convergent and elegant: Linoxepin (see picture), a new lignan with an unusual oxepin moiety, has been synthesized in only 10 steps. The protecting-group-free total synthesis includes a palladium- catalyzed Sonogashira reaction and a domino carbopalladation/Heck reaction of an allylsilane.

Get access to the full text of this article

Ancillary