509-64-8Relevant 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.
Claisen Reactions on Codeins. 8-Alkyl-8,14-dihydro-6-demethoxythebaines and -oripavines
Fleischhacker, Wilhelm,Richter, Bernd
, p. 3866 - 3880 (2007/10/02)
Claisen Eschenmoser reaction of 1a leads to 2a, which is transformed to 2c, e, and f by especially adopted reduction conditions.Reduction of 2i with LiAlH4 gives 2g.Catalytic hydrogenation of 2 results in ether bridge opening and formation of 4.Reaction of 2e with 4 N HCl yields the cyclic phenol 7a.Orthoester Claisen rearrangement of 1a leads to orthoacetate 10 and 11.Claisen Eschenmoser reaction on codeine isomers 1b and 12c gives the amides 12a and 1f.
Process for converting neopinone to codeinone
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, (2008/06/13)
A process for converting neopinone alkaloid to codeinone alkaloid which involves treating neopinone with a hydrohalic acid in a suitable solvent under anhydrous conditions. It also relates to the compound 8-halodihydrocodeinone hydrohalide.