Ring A of Ambruticin, in derivatized form (88), and a ring B derivative (93) were synthesized and used to determine the absolute stereochemistry of Ambruticin. The critical step that served to fix the stereochemistry in ring A could not be repeated on another system. Phosphonate 46 allowed the three-carbon homologation of aldehydes to conjugated ketene dithioacetals, but these could not be hydrolyzed. The resolution of 2-acetoxyaldehydes by 1-ephedrine was generalized, and an attempt was made to rationalize the behaviour of the intermediate oxazolidines, and to settle the controversy over their C(,2)-configurations.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.68719 |
| Date | January 1982 |
| Creators | Potvin, Pierre Guillame |
| 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: 000137871, proquestno: AAINL10281, Theses scanned by UMI/ProQuest. |
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