The Chemistry of Lycopodine

Abstract

Hydride reductions of a-cyanobromolycopodine and simple derivatives provided a number of derivatives of these compounds useful for oxidation and dehydrogenation studies. Dehydrogenation of a-des-tetrahydrolycrodine yielded a quinoline derivative. This result together with other evi­dence indicated that three of the four rings of lycopodine are six-membered. Two conjugated enols were isolated from oxidation experiments on a -cyanlyopodine. This indi­cated the presence of an active methylene group and from examination of these enols it appears unlikely that the carbonyl and nitrogen can be in the same ring. A benzal derivative was prepared from a-cyanolycopodine. This derivative was converted into a tertiary base which under­-went a bond scission reaction with methyl sulfate. A selenium dioxide oxidation product of benzal-a -cyanolyco-podine gave some indication of the relationship of the car­bonyl to the nitrogen in lycopodlne.