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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry