Two series of stable palladium and silver complexes ligated to hemilabile ligands were prepared. The stability and applicability of these well-defined complexes in promoting various reactions (cycloaddition, hydroamination, cross-coupling reactions, etc.) was investigated. Structure-activity studies with a series of related ligands led us to find a pronounced ligand effect on these reactions.
The dichotomous reactivity of triethyl phosphonium hydrobromide salt with dialkyl acetals was used for the synthesis of alkoxy phosphonium salts. Reactivity and applications of these phosphonium salts were described for the synthesis of the biologically active cinnamyl triazoles and ethyl indole-2-carboxylates. Total synthesis of the natural product nostodione A, was developed in eight chemical steps and with 21.6% overall yield from ethyl-2-indolecarboxylates. The synthesis of a mini-panel of structural analogs allowed for the discovery of anti-parasitic biological activity of nostodione A and its analogues for the first time. / Thesis / Doctor of Science (PhD)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/16600 |
| Date | 06 January 2015 |
| Creators | Keskar, Kunal |
| Contributors | McNulty, James, Chemistry and Chemical Biology |
| Source Sets | McMaster University |
| Language | English |
| Detected Language | English |
| Type | Thesis |
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