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-fonnyl-10-methoxyhexahydroaporphine molecule in essentially quantitative yield. Structural verification of the final product was through 13C 1H and NMR and X-ray crystallography.
ASJC Scopus subject areas
- Organic Chemistry