A Facile Synthesis of 7-Methylenebicyclo-[3.3.1]nonan-3-one and its Transformation Leading to the Novel Tricyclic System, Protoadamantane
A practical synthesis of 7-methylenebicyclo[3.3.1]nonan-3-one 2 by the fragmentation of 1,3-adamantanediol 8, which was prepared effectively by the ruthenium-catalized oxyfunctionalization of 1-adamantanol 7, is described. Characteristic transannular cyclization of 2 leading to a novel tricyclic sys...
Gespeichert in:
| Veröffentlicht in: | Synthetic communications 1996-04, Vol.26 (8), p.1555-1562 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| Zusammenfassung: | A practical synthesis of 7-methylenebicyclo[3.3.1]nonan-3-one 2 by the fragmentation of 1,3-adamantanediol 8, which was prepared effectively by the ruthenium-catalized oxyfunctionalization of 1-adamantanol 7, is described. Characteristic transannular cyclization of 2 leading to a novel tricyclic system, 1-hydroxy-4-protoadamantanone 9, via the corresponding exo-epoxide 10 is also presented. |
|---|---|
| ISSN: | 0039-7911 1532-2432 |
| DOI: | 10.1080/00397919608003522 |