## Abstract **The right bicycle**: A concise formal synthesis of platencin was based on an efficient oxygen‐mediated palladium‐catalyzed cycloalkenylation of **1** to form a bicyclo[3.2.1]octane, and a deoxygenative rearrangement of tosylhydrazone **2** to construct the bicyclo[2.2.2]octane **3**.
Formal Total Synthesis of Platencin
✍ Scribed by Georgy N. Varseev; Martin E. Maier
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 348 KB
- Volume
- 121
- Category
- Article
- ISSN
- 0044-8249
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✦ Synopsis
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.magnified image
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