Communication

Total Synthesis and Structure Assignment of (+)-Hexacyclinol†

  1. John A. Porco Jr. Prof. Dr.1,
  2. Shun Su1,
  3. Xiaoguang Lei1,
  4. Sujata Bardhan1,
  5. Scott D. Rychnovsky Prof. Dr.2

Article first published online: 27 JUL 2006

DOI: 10.1002/anie.200602854

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 45, Issue 35, pages 5790–5792, September 4, 2006

Additional Information

How to Cite

Porco, J. A., Su, S., Lei, X., Bardhan, S. and Rychnovsky, S. D. (2006), Total Synthesis and Structure Assignment of (+)-Hexacyclinol. Angew. Chem. Int. Ed., 45: 5790–5792. doi: 10.1002/anie.200602854

Author Information

  1. 1

    Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847

  2. 2

    Department of Chemistry, University of California—Irvine, Irvine, CA 92697-2025, USA

  1. †

    We thank Mr. Andrew Germain (Boston University) for helpful discussions, Dr. Friedrich A. Gollmick (Leibniz Institute for Natural Products Research and Infection Biology—Hans-Knöll-Institute, Jena, Germany) for providing spectra of natural hexacyclinol, and Dr. Emil Lobkovsky (Cornell University) for X-ray crystal structure analysis. Financial support from the NIH (GM62842 and P50 GM067041), Bristol-Myers Squibb, Merck, and Novartis is gratefully acknowledged.

Publication History

  1. Issue published online: 31 AUG 2006
  2. Article first published online: 27 JUL 2006
  3. Manuscript Received: 18 JUL 2006

Funded by

  • NIH. Grant Numbers: GM62842, P50 GM067041
  • Bristol-Myers Squibb
  • Merck
  • Novartis

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Keywords:

  • antiproliferative agents;
  • cyclization;
  • natural products;
  • terpenoids;
  • total synthesis
Thumbnail image of graphical abstract

Structure assigned: The revised structure of (+)-hexacyclinol (1) proposed recently was confirmed following the total synthesis of the natural product. The synthesis was designed around the highly stereoselective Diels–Alder dimerization of an epoxyquinol monomer, followed by intramolecular acid-catalyzed cyclization.

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