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Total Synthesis and Structure Assignment of (+)‐Hexacyclinol

2006; Wiley; Volume: 45; Issue: 35 Linguagem: Inglês

10.1002/anie.200602854

1521-3773

John A. Porco, Shun Su, Xiaoguang Lei, Sujata Bardhan, Scott D. Rychnovsky,

Microbial Natural Products and Biosynthesis

Angewandte Chemie International EditionVolume 45, Issue 35 p. 5790-5792 Communication Total Synthesis and Structure Assignment of (+)-Hexacyclinol† John A. Porco Jr. Prof. Dr., John A. Porco Jr. Prof. Dr. porco@bu.edu Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorShun Su, Shun Su Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorXiaoguang Lei, Xiaoguang Lei Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorSujata Bardhan, Sujata Bardhan Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorScott D. Rychnovsky Prof. Dr., Scott D. Rychnovsky Prof. Dr. Department of Chemistry, University of California—Irvine, Irvine, CA 92697-2025, USASearch for more papers by this author John A. Porco Jr. Prof. Dr., John A. Porco Jr. Prof. Dr. porco@bu.edu Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorShun Su, Shun Su Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorXiaoguang Lei, Xiaoguang Lei Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorSujata Bardhan, Sujata Bardhan Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847Search for more papers by this authorScott D. Rychnovsky Prof. Dr., Scott D. Rychnovsky Prof. Dr. Department of Chemistry, University of California—Irvine, Irvine, CA 92697-2025, USASearch for more papers by this author First published: 31 August 2006 https://doi.org/10.1002/anie.200602854Citations: 67 † 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. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat 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. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z602854_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume45, Issue35September 4, 2006Pages 5790-5792 RelatedInformation