The preparation of allylsilanes by silylation of allylsulfones followed by the reductive cleavage of the silylated sulfones, is described. The use of this new methodology in the synthesis of polyenic compounds including cis and trans retinoic acid was reported. / The preparations and reactions of a series of aminomethyl substituted $ alpha$-allylsilyl anions with carbonyl electrophiles were studied. The stereoselectivity of these reactions was subject to solvents and temperature effects. For instance, the condensation of these anions with carbonyl electrophiles proceeded to give the corresponding E-homoallylic alcohols in benzene, but the same reactions at lower temperatures in the presence of dimethoxyethane leads to the formation of the Z- isomers preferentially. / A new method for the preparation of aminomethyl substituted allylsilane 1 via the hydrosilylation of a new allene was described. This allene was prepared using an improved method of elimination of $ beta$-hydroxyvinylsilanes. / A number of analogs of retinoic acid were synthesized for their use in the treatment of leukemia. Their syntheses were carried out using the Wittig reaction. Two series of these analogs showed reasonable biological activity in HL-60 and P19 screenings. A third series of compounds was inactive.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.41648 |
| Date | January 1993 |
| Creators | Labrecque, Denis |
| Contributors | Chan, T. H. (advisor) |
| 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: 001403516, proquestno: NN94651, Theses scanned by UMI/ProQuest. |
Page generated in 0.0015 seconds