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Synthesis and Characterization of a Novel Diels - Alder Adduct of Codeine.
- Source :
-
Helvetica chimica acta [Helv Chim Acta] 2010 Feb; Vol. 93 (2), pp. 220-226. - Publication Year :
- 2010
-
Abstract
- The Diels - Alder reaction was applied to 4,5-epoxymorphinan opioids to generate a novel aromatic cycloadduct at C(7) - C(8): Thermolytic cleavage of sultine 8 produced the reactive diene o-quinodimethane 7 which condensed favorably with codeine (11), but not with codeinone (9) or 14- hydroxycodeinone (10), producing the desired tetrahydronaphtho adduct 12 with (7R,8R) geometry (Scheme). The configuration of the cycloadduct was determined by 1D- and 2D-NMR experiments. The unanticipated reactivity of these codeine derivatives was investigated by quantum-mechanical calculations, and it was determined that steric effects of the 6-keto and 14-hydroxy group likely precluded condensation by raising the molecular energy of their respective transition states.
Details
- Language :
- English
- ISSN :
- 0018-019X
- Volume :
- 93
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Helvetica chimica acta
- Publication Type :
- Academic Journal
- Accession number :
- 23378668
- Full Text :
- https://doi.org/10.1002/hlca.200900234