Enantioselective Synthesis of Oasomycin A, Part III: Fragment Assembly and Confirmation of Structure†
David A. Evans Prof.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorPavel Nagorny
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorKenneth J. McRae Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorLouis-Sebastian Sonntag Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorDominic J. Reynolds Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorFilisaty Vounatsos Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorDavid A. Evans Prof.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorPavel Nagorny
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorKenneth J. McRae Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorLouis-Sebastian Sonntag Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorDominic J. Reynolds Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorFilisaty Vounatsos Dr.
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617–495–1460
Search for more papers by this authorFinancial support has been provided by the National Institutes of Health (GM-33327-19), the Merck Research Laboratories, Amgen, and Eli Lilly. A postdoctoral fellowship was provided to L.-S.S. by the Deutscher Akademischer Austauschdienst and the Novartis Foundation, and to D.J.R. by the Glaxo Foundation.
Graphical Abstract
Vom Einzelnen zum Ganzen: Die Totalsynthese des natürlichen Makrolids Oasomycin A wurde abgeschlossen. Zu den zentralen Fragmentverknüpfungen gehören eine anti-Felkin-selektive Aldoladdition (grün), Kociensky-Julia-Olefinierungen (rot) und eine konkurrierende Weinreb-Amid-Acylierung (blau). Die Nützlichkeit von 4,5-Diphenyloxazol als Carboxy-Ersatz und die zu einem späten Zeitpunkt durchgeführte Makrolactonisierung, die den 42-gliedrigen Makrocyclus von Oasomycin A liefert, werden ebenfalls beschrieben.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2007/z603652_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.
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