Abstract
Two structural isomers of bisnorargemonine, 3,9-dihydroxy-2,8-dimethoxy-N-methylpavinane (Ia) and 2,8-dihydroxy-3,9-dimethoxy-N-methylpavinane (Ib), were synthesized employing the Pictet-Gams modification of the Bischler-Napieralski cyclization to construct the required isoquinoline intermediates. These were quaternized to the methiodides, followed by partial reduction to the N-methyl-1,2-dihydroisoquinolines, which were then cyclized under acidic conditions to provide Ia and Ib. Comparison of the NMR spectra of Ia and Ib with similar compounds revealed interesting aspects of the spectral properties pertaining to this ring system.
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