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

页码：3892 / 3894

页数：3

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