Synthetic Approaches toward Monocyclic 3-Amino-β-lactams

ChemistryOpen. 2017 Jun 5;6(3):301-319. doi: 10.1002/open.201700051. eCollection 2017 Jun.

Abstract

Due to the emerging resistance against classical β-lactam-based antibiotics, a growing number of bacterial infections has become harder to treat. This alarming tendency necessitates continued research on novel antibacterial agents. Many classes of β-lactam antibiotics are characterized by the presence of the 3-aminoazetidin-2-one core, which resembles the natural substrate of the target penicillin-binding proteins. In that respect, this Review summarizes the different synthetic pathways toward this key structure for the development of new antibacterial agents. The most extensively applied methods for 3-amino-β-lactam ring formation are discussed, in addition to a few less common strategies. Moreover, approaches to introduce the 3-amino substituent after ring formation are also covered.

Keywords: 3-amino-β-lactams; Staudinger synthesis; cyclization; cycloaddition; reactivity.

Publication types

  • Review