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A Total Synthesis of (±)‐Codeine by 1,3‐Dipolar Cycloaddition
Author(s) -
Erhard Thomas,
Ehrlich Gunnar,
Metz Peter
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201007448
Subject(s) - nitrone , cycloaddition , codeine , phenol , bicyclic molecule , chemistry , organic chemistry , information retrieval , computer science , stereochemistry , morphine , medicine , pharmacology , catalysis
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.