The chemistry of thujone. XX. New enantioselective syntheses of Ambrox and epi-Ambrox
The development of a new synthetic approach to (−)-Ambrox® ( 37 ) and epi-Ambrox® ( 29 ) using thujone ( 1 ) as a chiral synthon, is presented. Thujone ( 1 ), a readily available starting material obtained from Western red cedar, can be efficiently converted to β-cyperone ( 2 ) and the latter is the...
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| Veröffentlicht in: | Canadian journal of chemistry 1997-08, Vol.75 (8), p.1136-1150 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The development of a new synthetic approach to (−)-Ambrox® (
37
) and epi-Ambrox® (
29
) using thujone (
1
) as a chiral synthon, is presented. Thujone (
1
), a readily available starting material obtained from Western red cedar, can be efficiently converted to β-cyperone (
2
) and the latter is then chemically elaborated to the key intermediate, the enone
6
. A carbonyl transposition of
6
to enone
9
also allows a formal synthesis of (−)-Polywood® (
18
). Keywords: thujone, β-cyperone, (−)-Ambrox®, epi-Ambrox®, synthesis. |
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| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v97-136 |