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

被引：44
|
作者：
Erhard, Thomas [1 ]
Ehrlich, Gunnar [1 ]
Metz, Peter [1 ]
机构：
[1] Tech Univ Dresden, Fachrichtung Chem & Lebensmittelchem, D-01069 Dresden, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 17期
关键词：
allylic transposition; Claisen rearrangement; dearomatization; nitrone cycloaddition; total synthesis; MORPHINE; ANNOUNCEMENT; CODEINE; ACIDS;
D O I：
10.1002/anie.201007448
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：3892 / 3894
页数：3
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