Abstract
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.
Original language | English (US) |
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Pages (from-to) | 3881-3887 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 49 |
Issue number | 21 |
DOIs | |
State | Published - Oct 1984 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry