Communication

Total Synthesis of Coralloidolides A, B, C, and E†

  1. Thomas J. Kimbrough2,
  2. Paul A. Roethle Dr.2,
  3. Peter Mayer Dr.1,
  4. Dirk Trauner Prof.1

Article first published online: 9 MAR 2010

DOI: 10.1002/anie.200906126

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 49, Issue 14, pages 2619–2621, March 29, 2010

Additional Information

How to Cite

Kimbrough, T., Roethle, P., Mayer, P. and Trauner, D. (2010), Total Synthesis of Coralloidolides A, B, C, and E. Angewandte Chemie International Edition, 49: 2619–2621. doi: 10.1002/anie.200906126

Author Information

  1. 1

    Department of Chemistry, University of Munich, Butenandtstrasse 5–13 (F4.086), 81377 Munich (Germany), Fax: (+49) 892-180-77972

  2. 2

    Department of Chemistry, University of California Berkeley, Berkeley, CA 94720 (USA)

  1. †

    This work was supported by a Novartis Young Investigator Award. We thank Dr. Michele D’Ambrosio (Università di Trento) for providing us with authentic samples of coralloidolides.

Publication History

  1. Issue published online: 23 MAR 2010
  2. Article first published online: 9 MAR 2010
  3. Manuscript Received: 30 OCT 2009

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Keywords:

  • biomimetic synthesis;
  • chemoselectivity;
  • furanocembranoids;
  • Lewis acids;
  • total synthesis

Graphical Abstract

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Mapping the matrix: Several coralloidolides, members of a Mediterranean branch of the furanocembranoid family of diterpenes, have been synthesized. The total syntheses include biomimetic transformations that often occur with high chemoselectivity, thus obviating the need for protecting-group manipulations. The fascinating reactivity of 2,5-diene-1,4-dione moieties was explored in detail.

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