Synthetic Morphinans and Hasubanans. Part IV. Total Synthesis of 3,14-Dihydroxyisomorphinans, 3-Methoxy-Δ8,14-morphinans, and 9α-Hydroxy-3-methoxyhasubanan

Abstract

The synthesis of a versatile intermediate 4a-(2-aminoethyl)-l,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene (3a) and its utilization in the synthesis of 9α-hydroxy-3-methoxy-17-methylhasubanan (10), 3,14-dimethoxy-17-methylisomorphinan (9l), various 14-hydroxyisomorphinans (9), and 3-methoxy-Δ^8,14-morphinan (11b) is described. A number of 17-alkyl-3,14-dihydroxyisomorphinans were prepared and tested for narcotic antagonist and analgesic activities in laboratory animals. Some of these new compounds have exhibited significant activities.