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- W2951482227 abstract "The reaction of Ox-glycyl chloride with a chiral imine derived from the combination of d-(R)-glyceraldehyde acetonide and protected d-threonine afforded optically active, highly functionalized cis-substituted β-lactams 11 and 12. These β-lactams provide versatile intermediates for the syntheses of biologically important carbacephalosporins, isooxacephems, and other multicyclic β-lactams. Desilylation and oxidation of 12 with Dess−Martin periodinane followed by intramolecular cyclization produced a novel tricyclic β-lactam 17 and a 1-(hydroxymethyl)-O-2-isocephem 18 with [6R,7R] absolute configuration. Removal of the Ox protecting group and acylation of 17 in a one-pot reaction followed by saponification furnished the target salt 24. Alternatively, reaction of phthaloylglycyl chloride with the chiral imine derived from the combination of l-(S)-glyceraldehyde acetonide and protected d-threonine gave only one enantiomeric azetidinone 27 in high yield. Further manipulation of 27 provided a new tricyclic β-lactam 39 with [6S,7S] absolute configuration which satisfies the stereochemistry typically required for antibacterial activity. This synthetic procedure provides a short, versatile and enantioselective method of preparing polycyclic β-lactams. Biological testing of these tricyclic β-lactams indicated that salt 39 has potential inhibitory activity against four typical strains of bacteria." @default.
- W2951482227 created "2019-06-27" @default.
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- W2951482227 date "1996-01-01" @default.
- W2951482227 modified "2023-10-16" @default.
- W2951482227 title "Enantioselective Total Syntheses of [6<i>R</i>,7<i>R</i>] and [6<i>S</i>,7<i>S</i>] Tricyclic β-Lactams" @default.
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- W2951482227 doi "https://doi.org/10.1021/jo951651u" @default.
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