A new method for the preparation of 1,5-disubstituted-1Z,4Z-pentadienes by the addition of alkenyl cuprates to vinyltriphenylphosphonium bromide followed by an aldehyde is described. This method is used for the syntheses of 6Z,9Z-heneicosadiene and 15,15-(diethyldithio)-13S-t-butyldiphenylsilyloxy-6Z,9Z,11E-pentadecatriene. Syntheses of $(-)$-(5R)-argentilactone and (+)-(5R)-goniothalamin are described. Model studies towards the synthesis of the novel antileukemic agent CI-920 were carried out.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.75443 |
| Date | January 1987 |
| Creators | O'Connor, Brian, 1961- |
| 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: 000550563, proquestno: AAINL44368, Theses scanned by UMI/ProQuest. |
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