5-Allyl-9-oxobenzomorphans. 3. Potent narcotic antagonists and analgesics-antagonists in the series of substituted 2',9.beta.-dihydroxy-6,7-benzomorphans

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Abstract
5-Allyl-2''-methoxy-2-methyl-9-oxo-6,7-benzomorphan methiodide was converted in a selective 2-step process to the corresponding 9.beta.-hydroxy intermediates, which were transformed via modified von Braun demethylation-acylation to amides. These were reduced and demethylated to give a series of 5-allyl-2'',9.beta.-dihydroxy-2-substituted 6,7-benzomorphans, some of which were highly potent narcotic antagonists and/or analgesics [in mice and rats]. The resolution of the most interesting compounds and pharmacological properties of the optical isomers were also described. Reduction of the double bond in certain compounds did not appreciably alter pharmacological profiles, while cyclization to the tetrahydrofuranobenzomorphans substantially reduced the level of activities.

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