The total synthesis of the biologically active, dextrorotatory enantiomer of 3-methyl-7(beta)-phenylacetamido-(DELTA)('3)-O-2-isocephem-4-carboxylic acid was accomplished. The key step involved the asymmetric cycloaddition of azidoacetyl chloride to the cinnamylidene Schiff base of protected D-threonine to generate the desired monocyclic cis (beta)-lactam diastereomer (9:1). The absolute configuration of the final product was confirmed by comparing its antimicrobial activity with that of the corresponding racemate. / The influence of (a) the (beta)-chiral center in the starting (alpha)-amino acid, (b) the bulk of the carboxylic acid and (c) the distribution of bulk throughout the imine on the stereochemical outcome of the reaction was studied. The absence of racemization during the cycloaddition was demonstrated by the use of deuterated precursors. The great potential of D-glucosamine derivatives as chiral templates in this reaction was clearly illustrated.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.68663 |
| Date | January 1982 |
| Creators | Tenneson, Sheila Muriel. |
| 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: 000150973, proquestno: AAINK60986, Theses scanned by UMI/ProQuest. |
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