Communication

Asymmetric Synthesis of Natural Product Inspired Tricyclic Benzopyrones by an Organocatalyzed Annulation Reaction†

  1. Herbert Waldmann Prof.1,2,
  2. Vivek Khedkar Dr.1,2,‡,
  3. Heiko Dückert Dipl.-Chem.1,2,‡,
  4. Markus Schürmann Dr.3,
  5. Iris M. Oppel Priv.-Doz. Dr.4,
  6. Kamal Kumar Dr.1,2

Article first published online: 25 JUL 2008

DOI: 10.1002/anie.200802413

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 36, pages 6869–6872, August 25, 2008

Additional Information

How to Cite

Waldmann, H., Khedkar, V., Dückert, H., Schürmann, M., Oppel, Iris M. and Kumar, K. (2008), Asymmetric Synthesis of Natural Product Inspired Tricyclic Benzopyrones by an Organocatalyzed Annulation Reaction. Angew. Chem. Int. Ed., 47: 6869–6872. doi: 10.1002/anie.200802413

Author Information

  1. 1

    Max Planck Institut für molekulare Physiologie, Otto-Hahn Strasse 11, 44227-Dortmund (Germany)

  2. 2

    Technische Universität Dortmund, Fachbereich Chemie, 44221 Dortmund (Germany), Fax: (+49) 231-133-2499

  3. 3

    Technische Universität Dortmund, Anorganische Chemie, 44221 Dortmund (Germany)

  4. 4

    Analytische Chemie, Ruhr-Universität Bochum, 44780 Bochum (Germany)

  1. ‡

    These authors contributed equally to this work.

  1. †

    This work was supported by the Ministry of Innovation, Science, Research, and Technology of North Rhine-Westphalia and the Europäischer Fonds für Regionale Entwicklung of the Europäische Union.

Publication History

  1. Issue published online: 20 AUG 2008
  2. Article first published online: 25 JUL 2008
  3. Manuscript Received: 23 MAY 2008

Funded by

  • Ministry of Innovation, Science, Research, and Technology of North Rhine-Westphalia
  • Europäischer Fonds für Regionale Entwicklung

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (297K)

Keywords:

  • annulation;
  • asymmetric catalysis;
  • cinchona alkaloids;
  • natural products;
  • zwitterions
Thumbnail image of graphical abstract

Going back to nature: Electron-deficient oxadienes and electron-poor acetylene carboxylates react in the presence of an organocatalyst to give natural product inspired tricyclic benzopyrones efficiently (up to 99 % yield) and stereoselectively (up to 87 % ee; see scheme). This efficient and operationally simple asymmetric annulation involves the generation of zwitterions from acetylene carboxylates.

View Full Article with Supporting Information (HTML) Get PDF (297K)