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. / Thesis / Doctor of Philosophy (PhD)

The ring opened in the formation of α-cyanobromolycopodine has been found to be six-membered or larger. The product of hydrogenation of β-cyanobromolycopodine in alkaline medium has been shown to be the cyclized compound, C17H24ON2, not β-cyanolycopodine, C17H26ON2, as thought previously. A study was made of the β-cyclized compound but it could not be ascertained whether it has a ketone or an enol-ether structure. The possibility of a β-piperidone structure for lycopodine is discussed / Thesis / Master of Science (MS)

A study has been made of the chemistry of lycopodine, the major alkaloid of several species of Lycopodium. From the information obtained, most of the peripheral structure of the lycopodine molecule can be deduced. A complete structure is proposed for the alkaloid. / Thesis / Doctor of Philosophy (PhD)

The structure of lycopodine was investigated in the neighbourhood of the carbonyl group. The results obtained enabled the elucidation of a large part of the peripheral structure of the alkaloid. / Thesis / Master of Science (MS)

<p> The biosynthesis of lycopodine was studied by feeding radioactive acetate, acetoacetato, lysine and pelletierine to Lycopodium tristachyum. Partial degration of the radioactive lycopodine recovered from these experiments revealed specific incorporation of these precursors. The labeling pattern obtained is discussed in the light of the two major blogenetic hypothesis advanced for the Lycopodium alkaloids. </p> <p> The results obtained disproved Conroy's polyacetate hypothesis. They are consistent with the hypothesis that regards these alkaloids derived from lysine and acetate. </p> / Thesis / Doctor of Philosophy (PhD)