Abstract
Because of a deep interest in the relationship between the chemical structure and pharmacological properties of emetine, a series of compounds possessing structures allied to the emetine structure, recently determined by Robinson, were prepared. Comparative examination of these compounds with natural emetine was carried out together with the examination of chemical properties. In the present paper, preparation of rac-C-bis(Nor)emetine which lacks the ethyl group in the 6-position of benzoquinolizine nucleus in emetine, is described. A bis-(amide), obtained by the selective bonding of lmole of methanetriacetic acid and 2 moles of veratrylamine, was taken as the fundamental material for skeletal formation. This amide was subjected to dehydration-cyclization to the imide, reduced to the corresponding piperidone compound, and the benzoquinolizin-ium salt formed by isoquinoline cyclization. Catalytic reduction of this salt yielded the objective compound.
