Photo-adducts of aldehydes and furan were transformed to substituted monocyclic oxetanes, using a modification of the Fraser-Reid-Mootoo glycosidation procedure, and the chemistry of these oxetanes was studied. The photo-adduct of 2-methylfuran and propionyloxyacetaldehyde was transformed in a one-pot reaction to oxetane 75a, which gave oxetanocin and its epimer as described. The coupling of various oxetanes of the type 75 to nitrogenous bases was also investigated. / During the course of this work, it was found that epoxides of the type 23 could be transformed into bicyclic nucleosides 91 and furanosides 93. Bicyclic nucleosides 99 were also prepared, again using a modified Fraser-Reid-Mootoo coupling procedure. / An investigation into the resolution of photo-adducts of aldehydes and furans was initiated.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.70281 |
| Date | January 1992 |
| Creators | Hambalek, Robert J. (Robert Josef) |
| 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: 001291384, proquestno: AAINN74602, Theses scanned by UMI/ProQuest. |
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