Morphine Alkaloids, Part 114 A. Stereohomogeneous Synthesis of N-Demethyl-N-Substituted-14-Hydroxydihydromorphines

Article abstract of DOI:10.1007/BF00817599

A new route for the stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines 2a-f has been elaborated, involving O-demethylation of the novel dihydrocodeine derivatives 6a-f, obtained upon alkylation of the hitherto unknown N-demethyl-14-hydroxydihydrocodeine (5). Keywords. 6α,14β-Diacetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphinan, N-demethylation of; 3,6α,14β-Triacetoxy-17-alkyl-4,5α-epoxymorphinan, N-demethylation of; 17-Alkyl-4,5α-epoxy-6α,14β-dihydroxy-3-methoxymorphinan, O-demethylation of; 4,5α-Epoxy-6α,14β-dihydroxy-3-methoxymorphinan, N-alkylation of.