Synthetic studies on taxanes: construction of the tricyclic skeleton on the basis of a [6+2] cycloaddition reaction

The stereoselective synthesis of a tricyclic model compound of taxane diterpenes was achieved. The eight-membered B ring was constructed on the basis of a [6+2] cycloaddition reaction of a dicobalt acetylene complex with an enol silyl ether of cyclohexanone. After conversion of the cobalt complex mo...

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Veröffentlicht in:Tetrahedron letters 2014-01, Vol.55 (5), p.1097-1099
Hauptverfasser: Hanada, Ryosuke, Mitachi, Katsuhiko, Tanino, Keiji
Format: Artikel
Sprache:eng
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Zusammenfassung:The stereoselective synthesis of a tricyclic model compound of taxane diterpenes was achieved. The eight-membered B ring was constructed on the basis of a [6+2] cycloaddition reaction of a dicobalt acetylene complex with an enol silyl ether of cyclohexanone. After conversion of the cobalt complex moiety to an epoxide and introduction of a 3-cyanopropyl group, the A ring was formed via an intramolecular cyclization reaction under basic conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.12.096