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

• Main Author: Ugolini, Antonio.
• Format: Others
• Language: en
• Published: McGill University 1981
• Subjects: Antibiotics > Synthesis.; Beta lactamases.
• Online Access: http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=77122

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.