467-08-3Relevant articles and documents
A total synthesis of (±)-codeine by 1,3-dipolar cycloaddition
Erhard, Thomas,Ehrlich, Gunnar,Metz, Peter
supporting information; experimental part, p. 3892 - 3894 (2011/06/24)
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.
The Structure of Methyldihydropseudocodeine Methyl Ether
Theuns, Hubert G.,Janssen, Richard H. A. M.,George, Albert V. E.,Biessels, Hubertus W. A.
, p. 1461 - 1477 (2007/10/02)
Methyldihydropseudocodeine methyl ether, the product reported from the Grignard reaction of methyl magnesiumiodide with pseudocodeine methyl ether, was shown to have no resemblance to dibenzazonine alkaloids, as suggested earlier.It still belongs to the morphinan alkaloids.Spectral analysis shows it to be 5,6-didehydro-3,8β-dimethoxy-7β,17-dimethyl-morphinan-4-ol (4).Another product of the reaction mentioned was shown to be epimeric at C-7 with compound (4), and to have structure (5).In the course of this work the ethanamine bridge of these compounds, as well as of thebaine and codeine, were studied. 13C N.m.r. chemical shifts were assigned for the morphinan alkaloids, related to this research.
On the analysis and the stability of codeine phosphate. Part 1: Detection and determination of codeine in the presence of degradation products
Gundermann,Pohloudek-Fabini
, p. 296 - 299 (2007/10/02)
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