A Total Synthesis of (±)-Codeine by 1,3-Dipolar Cycloaddition

Nitrone cycloaddition on a dearomatized bicyclic phenol enabled the facile construction of the correctly configured phenanthrene skeleton of codeine. Further steps yielded allopseudocodeine in a completely diastereoselective manner and finally (±)‐codeine by allylic transposition through the hydroly...

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Veröffentlicht in:	Angewandte Chemie International Edition 2011-04, Vol.50 (17), p.3892-3894
Hauptverfasser:	Erhard, Thomas, Ehrlich, Gunnar, Metz, Peter
Format:	Artikel
Sprache:	eng
Schlagworte:	allylic transposition Bridged Bicyclo Compounds - chemistry Claisen rearrangement Codeine - chemical synthesis Codeine - chemistry Cyclization dearomatization Molecular Structure Nitrogen Oxides - chemical synthesis Nitrogen Oxides - chemistry nitrone cycloaddition Phenols - chemistry Stereoisomerism total synthesis
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Beschreibung
Zusammenfassung:	Nitrone cycloaddition on a dearomatized bicyclic phenol enabled the facile construction of the correctly configured phenanthrene skeleton of codeine. Further steps yielded allopseudocodeine in a completely diastereoselective manner and finally (±)‐codeine by allylic transposition through the hydrolysis of chlorocodides.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201007448