Abstract
AbstractOxaellipticine has been synthesized from 1,4‐dimethyldibenzofuran, by converting it to the 2‐aldehyde, forming the Schiff's base with aminoacetaldehyde diethyl acetal, and cyclizing this with 105%superphosphoric acid. Alternatively, tetrahydrodimethyldibenzofuran was formylated mainly at the 3‐position, and the 3‐(2‐nitrovinyl) derivative of the 3‐aldehyde, by hydride reduction, then Bischler‐Napieralski cyclization of the 3‐(2‐formamidoethyl) derivative, afforded hexahydrooxaellipticine, which could be aromatized only in poor yield. Isooxaellipticine, the pyrido‐A' positional isomer, was similarly prepared from the nitrovinyl derivative of 1,4‐dimethyl‐2‐dibenzofurancarboxaldehyde, through cyclization of the formamidoethyl intermediate and aromatization of the dihydro product. Likewise, isothiaellipticine was obtained from 1,4‐dimethyl‐2‐dibenzothiophenecarboxaldehyde.
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