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Catalytic Asymmetric Dihydroxylation of Enamides and Application to the Total Synthesis of (+)‐Tanikolide

2010; Wiley; Volume: 49; Issue: 46 Linguagem: Inglês

10.1002/anie.201004328

1521-3773

Benoit Gourdet, Hon Wai Lam,

Marine Sponges and Natural Products

Angewandte Chemie International EditionVolume 49, Issue 46 p. 8733-8737 Communication Catalytic Asymmetric Dihydroxylation of Enamides and Application to the Total Synthesis of (+)-Tanikolide† Benoit Gourdet, Benoit Gourdet School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK), Fax: (+44) 131-650-6453 http://homepages.ed.ac.uk/hlam/index.htmlSearch for more papers by this authorDr. Hon Wai Lam, Dr. Hon Wai Lam [email protected] School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK), Fax: (+44) 131-650-6453 http://homepages.ed.ac.uk/hlam/index.htmlSearch for more papers by this author Benoit Gourdet, Benoit Gourdet School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK), Fax: (+44) 131-650-6453 http://homepages.ed.ac.uk/hlam/index.htmlSearch for more papers by this authorDr. Hon Wai Lam, Dr. Hon Wai Lam [email protected] School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK), Fax: (+44) 131-650-6453 http://homepages.ed.ac.uk/hlam/index.htmlSearch for more papers by this author First published: 30 September 2010 https://doi.org/10.1002/anie.201004328Citations: 47 † This work was supported by the European Commission (Project No. MEST-CT-2005-020744) and the University of Edinburgh. We thank the EPSRC National Mass Spectrometry Service Centre at the University of Wales, Swansea, for providing high-resolution mass spectra. 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 Asymmetric dihydroxylation of β,β′- disubstituted enamides afforded chiral tertiary-alcohol-containing α-hydroxyaldehydes and 1,2-diols with high enantioselectivity (see scheme). This method was applied to the total synthesis of the antifungal natural product (+)-tanikolide, as well as the synthesis of an intermediate en route to (S)-oxybutynin. 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_201004328_sm_miscellaneous_information.pdf3.8 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, Issue46November 8, 2010Pages 8733-8737 RelatedInformation