Communication

Total Synthesis and Absolute Configuration of the Guaiane Sesquiterpene Englerin A†

  1. Matthieu Willot Dr.1,
  2. Lea Radtke Dipl.-Chem.1,
  3. Daniel Könning Dipl.-Chem.1,
  4. Roland Fröhlich Dr.2,‡,
  5. Viktoria H. Gessner Dr.3,‡,
  6. Carsten Strohmann Prof. Dr.3,‡,
  7. Mathias Christmann Prof. Dr.1

Article first published online: 30 OCT 2009

DOI: 10.1002/anie.200905032

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 48, pages 9105–9108, November 16, 2009

Additional Information

How to Cite

Willot, M., Radtke, L., Könning, D., Fröhlich, R., Gessner, V., Strohmann, C. and Christmann, M. (2009), Total Synthesis and Absolute Configuration of the Guaiane Sesquiterpene Englerin A. Angewandte Chemie International Edition, 48: 9105–9108. doi: 10.1002/anie.200905032

Author Information

  1. 1

    TU Dortmund University, Organic Chemistry, Otto-Hahn-Str. 6, 44227 Dortmund (Germany), Fax: (+49) 231-755-5363

  2. 2

    University of Münster, Institute of Organic Chemistry, Corrensstr. 40, 48149 Münster (Germany)

  3. 3

    TU Dortmund University, Inorganic Chemistry, Otto-Hahn-Str. 6, 44227 Dortmund (Germany)

  1. ‡

    X-ray crystallography

  1. †

    We thank the Fonds der Chemischen Industrie for a Dozentenstipendium (M.C.), the DAAD for a research fellowship (M.W.), Symrise GmbH und Co. KG (Holzminden) for a generous donation of nepetalactone, and Dr. Hans-Dieter Arndt for support and helpful discussions.

Publication History

  1. Issue published online: 11 NOV 2009
  2. Article first published online: 30 OCT 2009
  3. Manuscript Received: 8 SEP 2009

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (324K)

Keywords:

  • antitumor agents;
  • natural products;
  • rearrangements;
  • terpenes;
  • total synthesis

Graphical Abstract

Thumbnail image of graphical abstract

Catnip craze: Nepetalactone, the psychoactive ingredient of catmint, was selected as starting material for the first enantioselective synthesis of englerin A. This cytotoxic guaiane sesquiterpene is a highly selective inhibitor (1–87 nM) of several renal cancer cell lines. The absolute configuration of this natural product was determined by total synthesis.

View Full Article with Supporting Information (HTML) Get PDF (324K)