STEREOSELECTIVE SYNTHESIS OF BETA-NALTREXOL, BETA-NALOXOL, BETA-NALOXAMINE, BETA-NALTREXAMINE AND RELATED-COMPOUNDS BY THE APPLICATION OF THE MITSUNOBU REACTION

As a continuation of our work, aimed at adopting the Mitsunobu reactio n in the morphine series, a few representatives of dihydroisocodeines and dihydroisomorphines and their 14 beta-hydroxy analogues were prepa red. p-Nitrobenzoic acid was used as carboxylic acid and the prepared esters were cleaved to obtain the title compounds. Using phthalimide a s acidic component several new 6 beta-phthalimidodihydromorphine and d ihydrocodeine derivatives and their 14 beta-hydroxy analogues have bee n synthesized. Cleavage of the phthalimido derivatives with hydrazine hydrate afforded the corresponding 6 beta-amino derivatives.