Galanthamine Chemistry. VII. Synthesis of Analogues of Galanthamine

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Abstract
4-Acetoxy-7"-methoxyspiro[cyclohexane-1,1"(2"H)-naphthalen]-4"(3"H)-one (XXIV) was synthesized and subjected to (he Schmidt reaction to give the isomertc benzazepinones. N-methylation followed by reduction with lithium aluminum hydride of these compounds afforded the 1- and 2-benzazepine. la contrast to the inhibitory effect of galanthamine on acetylcholinesterase, neither of these 2 synthetics showed appreciable anticholinesterase activity.

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