Enantioselective Synthesis of Oasomycin A, Part I: Synthesis of the C1–C12 and C13–C28 Subunits†
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 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 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 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 authorRisheng Xu
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 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 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 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 authorRisheng Xu
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.
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