Enantioselective Total Syntheses of Three Cladiellins (Eunicellins): A General Approach to the Entire Family of Natural Products
2010; Wiley; Volume: 49; Issue: 51 Linguagem: Inglês
10.1002/anie.201005508
ISSN1521-3773
AutoresJ. Stephen Clark, Raphaëlle Berger, Stewart T. Hayes, Lynne H. Thomas, Angus J. Morrison, Luca Gobbi,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAngewandte Chemie International EditionVolume 49, Issue 51 p. 9867-9870 Communication Enantioselective Total Syntheses of Three Cladiellins (Eunicellins): A General Approach to the Entire Family of Natural Products† Prof. Dr. J. Stephen Clark, Corresponding Author Prof. Dr. J. Stephen Clark [email protected] WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorRaphaëlle Berger, Raphaëlle Berger WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorDr. Stewart T. Hayes, Dr. Stewart T. Hayes School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (United Kingdom)Search for more papers by this authorDr. Lynne H. Thomas, Dr. Lynne H. Thomas WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorDr. Angus J. Morrison, Dr. Angus J. Morrison MSD, Newhouse, Lanarkshire, ML1 5SH (United Kingdom)Search for more papers by this authorDr. Luca Gobbi, Dr. Luca Gobbi Discovery Chemistry (PRCB), F. Hoffmann-La Roche Ltd, Pharmaceuticals Division, 4070 Basel (Switzerland)Search for more papers by this author Prof. Dr. J. Stephen Clark, Corresponding Author Prof. Dr. J. Stephen Clark [email protected] WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorRaphaëlle Berger, Raphaëlle Berger WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorDr. Stewart T. Hayes, Dr. Stewart T. Hayes School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (United Kingdom)Search for more papers by this authorDr. Lynne H. Thomas, Dr. Lynne H. Thomas WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorDr. Angus J. Morrison, Dr. Angus J. Morrison MSD, Newhouse, Lanarkshire, ML1 5SH (United Kingdom)Search for more papers by this authorDr. Luca Gobbi, Dr. Luca Gobbi Discovery Chemistry (PRCB), F. Hoffmann-La Roche Ltd, Pharmaceuticals Division, 4070 Basel (Switzerland)Search for more papers by this author First published: 16 November 2010 https://doi.org/10.1002/anie.201005508Citations: 45 † We thank the EPSRC, M.S.D. and F. Hoffmann-La Roche Ltd for financial support. 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 Graphical Abstract Stereoselective rearrangement of a free or metal-bound oxonium ylide, generated by rhodium-catalyzed intramolecular cyclization of the diazo ketone 1, afforded E-configured O-bridged bicyclic ether (E)-2, which was efficiently transformed into (−)-cladiella-6,11-dien-3-ol. TBS=tert-butyldimethylsilyl. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201005508_sm_miscellaneous_information.pdf1.4 MB miscellaneous_information 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. Volume49, Issue51December 17, 2010Pages 9867-9870 RelatedInformation
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