Health & Environmental Research Online (HERO)


Print Feedback Export to File
8269711 
Journal Article 
A total synthesis of (±)-codeine by 1,3-dipolar cycloaddition 
Erhard, T; Ehrlich, G; Metz, P 
2011 
Yes 
Angewandte Chemie (International Edition)
ISSN: 1433-7851
EISSN: 1521-3773 
50 
17 
3892-3894 
English 
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. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 
allylic transposition; Claisen rearrangement; dearomatization; nitrone cycloaddition; total synthesis