Communication

Total Synthesis and Structural Revision of Callipeltoside C

  1. Joseph Carpenter1,2,
  2. Alan B. Northrup1,2,
  3. deMichael Chung Dr.1,2,
  4. John J. M. Wiener1,2,
  5. Sung-Gon Kim Dr.1,2,
  6. David W. C. MacMillan Prof.1,2

Article first published online: 1 APR 2008

DOI: 10.1002/anie.200800086

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 19, pages 3568–3572, April 28, 2008

Additional Information

How to Cite

Carpenter, J., Northrup, Alan B., Chung, d., Wiener, John J. M., Kim, S.-G. and MacMillan, David W. C. (2008), Total Synthesis and Structural Revision of Callipeltoside C. Angew. Chem. Int. Ed., 47: 3568–3572. doi: 10.1002/anie.200800086

Author Information

  1. 1

    Merck Center for Catalysis, Princeton University, Washington Road, Princeton NJ 08544-1009, USA, http://www.princeton.edu/∼dmacgr/

  2. 2

    Department of Chemistry, Caltech, 1200 East California Boulevard, Pasadena CA 91125, USA, Fax: (+1) 609-258-5922

Publication History

  1. Issue published online: 21 APR 2008
  2. Article first published online: 1 APR 2008
  3. Manuscript Received: 8 JAN 2008

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Keywords:

  • asymmetric synthesis;
  • callipeltoside C;
  • carbohydrates;
  • organocatalysis
Thumbnail image of graphical abstract

Look again: Highlights of the 20-step synthesis of callipeltoside C include the proline-catalyzed direct aldol reaction, enantioselective α-oxyamination reaction, and rapid access to the carbohydrate framework using a de novo synthesis protocol. Based on this work the previously assigned absolute configuration of the pendent 2-O-methylevalose unit has been revised.

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