New methods for the synthesis of spirocyclic cephalosporin analogues

Dataset

Abstract

Spiro compounds provide attractive targets in drug discovery due to their inherent three-dimensional structures, which enhance protein interactions, aid solubility and facilitate molecular modelling. However, synthetic methodology for the spiro-functionalisation of important classes of penicillin and cephalosporin β-lactam antibiotics is comparatively limited. We report a novel method for the generation of spiro-cephalosporin compounds through a Michael-type addition to the dihydrothiazine ring. Coupling of a range of catechols is achieved under mildly basic conditions (K2CO3, DMF), giving the stereoselective formation of spiro-cephalosporins (d.r. 14:1 to 8:1) in moderate to good yields (28-65%).

Data Citation

Hulme, Alison; Zhao, Alan; Horsfall, Louise. (2021). New methods for the synthesis of spirocyclic cephalosporin analogues, [dataset]. University of Edinburgh. School of Chemistry. https://doi.org/10.7488/ds/3144.
Date made available1 Oct 2021
PublisherEdinburgh DataShare
Geographical coverageUK,UNITED KINGDOM

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