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Synthesis on some new-l-lactam antibiotics : a thesis

The syntheses of the cephalosporin analogs cis-N-(2'-hydroxyphenyl)-3-phenylacetamido-4-hydroxymethyl-2-azetidinone (37), cis-N-(2'-hydroxy-5'-nitrophenyl)-3-phenylacetamido-4-hydroxymethyl-2-azetidinone (59) and 7-(beta)-phenylacetamido-3'-hydroxybenzo{3,4}-0,2-isocephem (77) are described. Compounds 37 and 59 were devoid of antibacterial activity, while (beta)-lactam 77 showed weak activity against two micoorganisms. / Two new ring systems, 2-phenylcarbapenams 146 and 157 have been prepared. These are key intermediates in the syntheses of phosphonic acid carbapenam 148 and the carboxylic acid derivative 158, respectively. / The one carbon homologation of (beta)-trimethylsilyl-(alpha),(beta)-unsaturated esters with diazomethane was extended to the corresponding (beta)-trimethylsilyl or (beta)-t-butyldimethylsilyl aldehydes.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.77122
Date January 1981
CreatorsUgolini, Antonio.
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: 000139111, proquestno: AAINK54926, Theses scanned by UMI/ProQuest.

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