Synthesis and analgesic activity of pyrrolidinomorphinan derivatives

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Diels-Alder reactions of (-)-thebaine with N-substituted maleimides have been used to obtain cycloadducts possessing α-facial stereoselectivity. The 3-O-and 6-O-demethylated derivatives as well as the products of complete and partial reduction of carbonyl groups in the pyrrolidinedione moiety were also obtained. Some of the synthesized compounds have proved to be promising analgesics. The introduction of the bromine atom into the aryl moiety favors prolongation of the analgesic effect.

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