Abstract
In this thesis, I developed a synthetically valuable reaction of various 3-trimetylsilyl enol acetates that is induced by silicon under thermal conditions. I also synthesized the glycosylated nordihydroguaiaretic acid (NDGA) derivatives to act as a new class of anti-caner agents. Furthermore, new nanomaterials were synthesized as a novel DNA cross-linking agent. In part 1 of this thesis, I reported the success in utilizing the electronic effect of silicon to induce an ene-type reaction. Five enolate substrates with varied structural complexity were successfully oxidized to the corresponding enones in satisfactory yields (51–77%). The electronic stabilizing effect of silicon (□ or □ effect) on a carboradical intermediate plays a vital role in the induction of this new ene-type reaction. In part 2, I synthesized five new NDGA derivatives, among them two contain different lengths of triazole-linkage without any sugar moiety, and the other three containing different triazole-length linkage with galactose or glucose moiety. The effects of glucosyl or galactosyl derivatives were showed suppression of growth rate in Hep 3B cell lines at the dose levels higher than 60 □M. The resultant NDGA derivatives with sugar units could greatly increase the solubility in water. In part 3, I successfully prepared new biological materials conjugate the N-hydroxymethyl-phthalimide on the iron oxide. Each Fe3O4 nanopartiles was with diameter 6.1 □ 0.8 nm by TEM and UV light could be as a trigger to release formaldehyde. This nanomaterial improved the cross-linking potency at low concentration because of the high local density.