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Paper | Regular issue | Vol 36, No. 7, 1993, pp.1509-1519
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6305
Synthesis of N-Demethyl-N-substituted 14β-Hydroxy isomorphine and Dihydroisomorphine Derivatives

Sándor Hosztafi, Csaba Simon, and Sándor Makleit*

*Department of Organic Chemistry, Lajos Kossuth University, P.O.Box 20, H-4010 Debrecen, Hungary


Some new representatives (3e-3h, 5g) of a new group of structurally related morphine-agonist and antagonist compounds have been prepared in stereochemically homogeneous forms. Application of the Mitsunobu-reaction for suitable codeine derivatives (1a-1d) gave the benzoates (2a-2d) of the hitherto unknown C-6 iso-compounds, which were converted into the desired isocodeines (3b-3d) by means of alkaline hydrolysis. O-Demethylation of these derivatives afforded the corresponding morphine analogues. The preparation of 3e was also carried out from 1f via compound (2e). A hitherto unknown N-demethylation also allowed the conversion of 3a and 5a into the target compounds. With the exception of N-allyl derivatives, the dihydro analogues were obtained by the hydrogenation of the C7-C8 double bond.