Communication

Total Synthesis, Configuration, and Biological Evaluation of Anguinomycin C†

  1. Simone Bonazzi MSc1,
  2. Stephan Güttinger Dr.2,
  3. Ivo Zemp Dipl.-Natw.2,
  4. Ulrike Kutay Prof. Dr.2,
  5. Karl Gademann Prof. Dr.1

Article first published online: 4 OCT 2007

DOI: 10.1002/anie.200703134

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 46, Issue 45, pages 8707–8710, November 19, 2007

Additional Information

How to Cite

Bonazzi, S., Güttinger, S., Zemp, I., Kutay, U. and Gademann, K. (2007), Total Synthesis, Configuration, and Biological Evaluation of Anguinomycin C. Angew. Chem. Int. Ed., 46: 8707–8710. doi: 10.1002/anie.200703134

Author Information

  1. 1

    Chemical Synthesis Laboratory (SB-ISIC-LSYNC), Swiss Federal Institute of Technology (EPFL), 1015 Lausanne, Switzerland, Fax: (+41) 21-693-9700 http://isic.epfl.ch/lsync

  2. 2

    Institut für Biochemie, Swiss Federal Institute of Technology (ETH Zürich), 8093 Zürich, Switzerland

  1. †

    We thank the Swiss National Science Foundation for support (Projects 200021-115918/1 (K.G.) and 3100A0-101712 (U.K.)), as well as the Latsis Foundation. This work is part of the planned PhD thesis of S.B. at ETH Zürich. We thank Dr. B. Schweizer and Dr. R. Scopelliti for X-ray structural analyses.

Publication History

  1. Issue published online: 8 NOV 2007
  2. Article first published online: 4 OCT 2007
  3. Manuscript Received: 13 JUL 2007

Funded by

  • Swiss National Science Foundation. Grant Numbers: 200021-115918/1, 3100A0-101712

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Keywords:

  • antitumor agents;
  • leptomycins;
  • nuclear export;
  • polyketides;
  • total synthesis
Thumbnail image of graphical abstract

Against nuclear export! Immunofluorescence assays indicate that anguinomycin C is a potent inhibitor of protein export from the nucleus. Key features in the total synthesis of this antitumor natural product include a Cr-catalyzed enantioselective hetero-Diels–Alder reaction, a Negishi reaction with stereoinversion, and application of the DIOZ auxiliary.

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