466-96-6Relevant articles and documents
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Folkers
, p. 1815 (1936)
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A total synthesis of (±)-codeine by 1,3-dipolar cycloaddition
Erhard, Thomas,Ehrlich, Gunnar,Metz, Peter
, 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.
