The investigations whose results are reported in this Thesis involved the synthesis of variously functionalized p-methane based epoxides, hydroxylated derivatives, β-amino alcohols, β-hydroxy sulphides and C-gycosidic compounds. These compounds bearing a similar skeleton motif were evaluated to determine their efficacy as mosquito repellents and their apoptosis inducing potential. Twelve epoxides obtained via reactions with bicarbonate activated peroxide (BAP) meta-chloroperoxybenzoic acid (m-CPBA), and via bromohydrin formation exhibited good to high mosquito repellence, some of which were more active than p-menthane-3,8-diol which was used as the standard insecticide in this study. The epoxides also exhibited good to excellent apoptosis inducing potential against two cell lines (Jurkat T and CHO) and six indicated better activity than Camptothecin, a drug that was used as the standard. Seven variously substituted hydroxylated compounds were obtained via oxymercuration-demercuration and cishydroxylation reactions using OsO4, which revealed varying levels of mosquito (Anopheles gambiae) repellence, ranging from poor to very high repellent activity. The hydroxylated derivatives also indicated some level of apoptosis induction. Eight variously substituted β-amino alcohols and nine β-hydroxysulphides were obtained via oxirane ring opening with benzylamine, aniline, piperidine and benzylmercaptan also indicated some level of apoptosis induction. C-glycosylation catalyzed by TiCl4 afforded six C-glycals, which also exhibited varying levels of apoptotic induction potential. Structures of the synthesized compounds were established based on analysis of spectroscopic data.

A Thesis Submitted in Fulfillment of the Requirement for the Degree of Doctor of Philosophy (Chemistry)