The formation of the indolizidine ring system was studied. First, the intramolecular electrophilic cyclisation of substituted allylsilanes, vinylsilanes and enol ethers was attempted. Reactions with the allylsilane moiety indeed gave the desired ring system, whereas the vinylsilanes failed to give any cyclisation product. In order to easily introduce oxygen functionalities in the rings, enol ether cyclisations were also attempted but did not produce the expected bicyclic systems. / Secondly, the intramolecular nucleophilic cyclisation of free amines bearing suitable leaving groups was attempted, providing an easy method for the formation of the indolizidine system, with an interesting entry into the synthesis of biologically active polyhydroxylated alkaloids Swainsonine and Castanospermine. The synthesis of these two natural compounds, as well as some of their analogues, using the successful nucleophilic methodology was attempted. / Finally, the regioselective and stereoselective introduction of hydroxyl groups into the pyrrolidine ring system was studied in order to prepare mono- and di-hydroxylated pyrrolidines for the synthesis of the aforementioned natural products.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.70343 |
| Date | January 1991 |
| Creators | St-Denis, Yves |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001271106, proquestno: AAINN74913, Theses scanned by UMI/ProQuest. |
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