Constitution of Strychnine and its Relation to Cinchonine

Abstract

THE progress of experimental studies of strychnine derivatives, especially of neostrychnine, in this Laboratory has shown that no formulation hitherto suggested is adequate. Furthermore, it has not been found possible to modify the structure in a satisfactory manner on the basis of generally accepted deductions in regard to the ring containing the amide group. The validity of the simple and direct explanations of Leuchs' degradation of the strychninolones and brucinolones has therefore become questionable, and feasible alternatives of a more complicated character have been devised. These allow the amide ring to be five-membered, and on this basis an entirely novel and very satisfactory strychnine constitution (I) can be developed. This serves to illustrate the whole chemistry of the alkaloids, including the most recent findings, and must therefore be regarded as the best working hypothesis at present available. It is free from all stereochemical difficulty, and double bonds can be accommodated where necessary.