A novel and stereocontrolled synthesis of (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid, a potent broad spectrum β-lactamase inhibitor

Autor:	Nigel J. P. Broom, Graham Walker, Steven Coulton, John Barry Harbridge, Neal Frederick Osborne, Irene Stirling-François, Michael A. Harris
Rok vydání:	1989
Předmět:	Acylation chemistry.chemical_classification Broad spectrum Deprotonation β lactamase inhibitor Chemistry Stereochemistry Carboxylic acid Molecular Medicine Reductive elimination
Zdroj:	J. Chem. Soc., Chem. Commun.. :371-373
ISSN:	0022-4936
DOI:	10.1039/c39890000371
Popis:	The key step in the preparation of the title compound (BRL 42715) from 6-aminopenicillanic acid was the condensation of the anion, generated by deprotonation of p-methoxybenzyl (5R,6S)-6-bromopenem-3-carboxylate(10), with 1-methyl-1,2,3-triazole-4-carbaldehyde; in situ acylation, followed by reductive elimination afforded the isomeric (Z)- and (E)-6-triazolylmethylene penem esters, (12) and (13) respectively.
Databáze:	OpenAIRE
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