A general method of transforming aldehydes via $ alpha$,$ beta$-unsaturated esters to the 3-substituted glutarimide ring was developed and was applied to the construction of ring A of $(-)$-sesbanimide A (1) and the AB ring moiety of (+)-sesbanimide A (2). The phase-transfer-catalyzed methylenation reaction of dihydroxy dithioacetal 46 brought about a 1,4-migration of the t -butyldiphenylsilyl group to provide 1,3-dioxolane derivative 49. / Model studies towards the synthesis of (+)-sesbanimide (2) and C-15 desmethyl sesbanimide 93 were carried out using allylsilanes 74, 79 and 94, with aldehydes 56a and 85. / The synthesis of 8- O -benzyl-13- O-t -butyldimethylsilyl sesbanimides 88, 13-deoxychloro sesbanimide 89, 8- O -benzyl-13- O - t -butyldimethylsilyl-15-desmethyl sesbanimide 91, 13-deoxychloro-15-desmethyl sesbanimide 92, 8- O -benzyl-13- O - t -butyldiphenylsilyl-15-desmethyl sesbanimide 96 and 13- O - t -butyldiphenylsilyl-15-desmethyl sesbanimide 97 are described.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.75454 |
| Date | January 1987 |
| Creators | Tan, Charles Chu |
| 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: 000554191, proquestno: AAINL44443, Theses scanned by UMI/ProQuest. |
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