Sequential Benzylic Oxidation of Naloxone 3-Methyl Ether
Naloxone 3-methyl ether was selectively oxidized by treatment with cerium ammonium nitrate in aqueous acetonitrile at ambient temperature to provide the 10-(S)-hydroxy adduct. The stereochemistry of the oxidation product was proven by single crystal X-ray structure determination. The Dess-Martin per...
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| Veröffentlicht in: | Synthetic communications 2000-12, Vol.30 (24), p.4513-4521 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | Naloxone 3-methyl ether was selectively oxidized by treatment with cerium ammonium nitrate in aqueous acetonitrile at ambient temperature to provide the 10-(S)-hydroxy adduct. The stereochemistry of the oxidation product was proven by single crystal X-ray structure determination. The Dess-Martin periodinane further oxidized the 10-hydroxy to the 10-keto analog. Deprotection formed 10-ketonaloxone as an analytical reference standard. |
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| ISSN: | 0039-7911 1532-2432 |
| DOI: | 10.1080/00397910008087081 |