The chemistry of thujone. XVIII Homothujone and its derivatives
The monoterpene thujone ( 1 ) is ring expanded regioselectively to provide homothujone ( 4 ) in order to explore its potential as a chiral starting material. Stereoselective Robinson annulation of homothujone provides an enone intermediate ( 5 ), further derivatization of which was undertaken to fur...
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| Veröffentlicht in: | Canadian journal of chemistry 1996-05, Vol.74 (5), p.666-676 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The monoterpene thujone (
1
) is ring expanded regioselectively to provide homothujone (
4
) in order to explore its potential as a chiral starting material. Stereoselective Robinson annulation of homothujone provides an enone intermediate (
5
), further derivatization of which was undertaken to furnish functionalized naphthalenones useful for synthesis of the antifeedant (−)-polygodial and the ambergris fragrance (−)-Ambrox®. Key words: thujone, homothujone, synthesis, naphthalenones, polygodial, Ambrox. |
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| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v96-072 |