Studies in the Synthesis of C Ring Bridged Morphinans. 2.¹ The Synthesis and Structural Verification of a Novel 3, llc-Ethano-10-hydroxy-6-methyl-l, 2, 3, 3a, llb, llc-hexahydroaporphine

The title compound and its 10-methoxy congener were prepared from bicyclo[2.2.2]oct-2-ene in approximately 2% overall yield. In the course of the synthesis of the final product, 14 novel bicyclo[2.2.2]- and -[3.2.1]octane derivatives were isolated and characterized. Entry into the aporphine ring system was accomplished by cyclizing the appropriate N-formylisoquinoline precursor with liquified hydrofluoric acid which gave the bridged 6-formyl-10-methoxyhexahydroaporphine molecule in essentially quantitative yield. Structural verification of the final product was through ¹³C and ¹H NMR and X-ray crystallography.