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Radical reactions in organic synthesis

The 4-substituted glutarimide required for the synthesis of sesbanimide (53) was obtained by free radical addition of iodoacetamide onto the $ alpha, beta$-unsaturated ester (81) mediated by tributyltin; the lactol ring C was prepared by the analogous free radical cyclization of the $ alpha$-bromo-dipropargyl ketal 73. / The syntheses of tricyclic carbapenems involved appropriately substituted monocyclic azetidinone precursors. Free radical 5- exo cyclizations led to the relatively unstable benzo carbapenems 116, 119 and 120. The 6- exo mode, however, afforded stable benzo carbacephems 125, 127, 132 and 133. / $ alpha$-Bromo- and $ alpha{,} alpha$-dibromoazetidinones were converted stereoselectively to the $ alpha$-alkylazetidinones 149 and 153, or to $ beta$-alkylazetidinones 151, 154 and 159 by a free radical addition onto olefins 148 or allyltributyltin.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.75340
Date January 1986
CreatorsSacripante, Guerino.
PublisherMcGill University
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
LanguageEnglish
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Formatapplication/pdf
CoverageDoctor of Philosophy (Department of Chemistry.)
RightsAll items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated.
Relationalephsysno: 000416946, proquestno: AAINL38158, Theses scanned by UMI/ProQuest.

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