Synthesis and Reactions of the Pestalotiopsin Skeleton
2008; Wiley; Volume: 47; Issue: 30 Linguagem: Inglês
10.1002/anie.200801900
ISSN1521-3773
AutoresThomas Baker, David J. Edmonds, Deborah Hamilton, Christopher J. O’Brien, David J. Procter,
Tópico(s)Chemical synthesis and alkaloids
ResumoAngewandte Chemie International EditionVolume 47, Issue 30 p. 5631-5633 Communication Synthesis and Reactions of the Pestalotiopsin Skeleton† Thomas M. Baker, Thomas M. Baker School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4939Search for more papers by this authorDavid J. Edmonds Dr., David J. Edmonds Dr. Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ (UK)Search for more papers by this authorDeborah Hamilton, Deborah Hamilton School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4939Search for more papers by this authorChristopher J. O'Brien Dr., Christopher J. O'Brien Dr. Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ (UK)Search for more papers by this authorDavid J. Procter Dr., David J. Procter Dr. [email protected] School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4939Search for more papers by this author Thomas M. Baker, Thomas M. Baker School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4939Search for more papers by this authorDavid J. Edmonds Dr., David J. Edmonds Dr. Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ (UK)Search for more papers by this authorDeborah Hamilton, Deborah Hamilton School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4939Search for more papers by this authorChristopher J. O'Brien Dr., Christopher J. O'Brien Dr. Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ (UK)Search for more papers by this authorDavid J. Procter Dr., David J. Procter Dr. [email protected] School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL (UK), Fax: (+44) 161-275-4939Search for more papers by this author First published: 09 July 2008 https://doi.org/10.1002/anie.200801900Citations: 39 † This work was supported by EPSRC, Leverhulme Trust, University of Manchester, University of Glasgow, Merck Sharp & Dohme, AstraZeneca, and Pfizer. 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 onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Family ties: The pestalotiopsin framework has been constructed by using a SmI2-mediated cyclization and a Nozaki–Hiyama–Kishi coupling to construct the four- and nine-membered rings of the target, respectively. The first synthetic entry into the previously unexplored taedolidol family of natural products has been achieved through a stereoselective, acid-mediated cyclization of the pestalotiopsin skeleton. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z801900_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. References 1 1aM. Pulici, F. Sugawara, H. Koshino, J. Uzawa, S. Yoshida, E. 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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. 16Attempts to invert the configuration at C7 by using Mitsunobu conditions led to elimination of the secondary hydroxy group. Citing Literature Volume47, Issue30July 14, 2008Pages 5631-5633 ReferencesRelatedInformation
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