Formal Total Synthesis of Platencin†
Georgy N. Varseev Dipl.-Chem.
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen (Germany), Fax: (+49) 7071-295-137, http://www.uni-tuebingen.de/uni/com/welcome.htm
Search for more papers by this authorMartin E. Maier Prof. Dr.
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen (Germany), Fax: (+49) 7071-295-137, http://www.uni-tuebingen.de/uni/com/welcome.htm
Search for more papers by this authorGeorgy N. Varseev Dipl.-Chem.
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen (Germany), Fax: (+49) 7071-295-137, http://www.uni-tuebingen.de/uni/com/welcome.htm
Search for more papers by this authorMartin E. Maier Prof. Dr.
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen (Germany), Fax: (+49) 7071-295-137, http://www.uni-tuebingen.de/uni/com/welcome.htm
Search for more papers by this authorFinancial support by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie is gratefully acknowledged. We thank Graeme Nicholson for HRMS measurements and analytical GC on a chiral phase.
Abstract
Der richtige Bicyclus: Die effiziente sauerstoffvermittelte palladiumkatalysierte Cycloalkenylierung von 1 zu einem Bicyclo[3.2.1]octan und die desoxygenierende Umlagerung des Tosylhydrazons 2 zum Bicyclo[2.2.2]octan 3 sind wesentliche Schritte der Synthese der Kernstruktur 4 von Platencin, deren Gesamtausbeute nach 13 Stufen ausgehend von einer käuflich erhältlichen Verbindung 17.5 % betrug. Ts=p-Toluolsulfonyl, TBS=tert-Butyldimethylsilyl, Piv=Pivaloyl.
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