Synthesis of 2-fluoro-6-O-propargyl-11,15-carbamate ketolides. A novel class of antibiotics

Authors
Phan, LT Clark, RF Rupp, M Or, YS Chu, DTW Ma, Z
Citation
Lt. Phan et al., Synthesis of 2-fluoro-6-O-propargyl-11,15-carbamate ketolides. A novel class of antibiotics, ORG LETT, 2(19), 2000, pp. 2951-2954
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
19
Year of publication
2000
Pages
2951 - 2954
Database
ISI
SICI code
1523-7060(20000921)2:19<2951:SO2KAN>2.0.ZU;2-7
Abstract
[GRAPHICS] A novel class of 2-fluoro-6-O-propargyl-11,12-carbamate ketolide derivative s of erythromycin has been synthesized for antibacterial SAR studies. Repla cement of the C2-hydrogen by a fluorine atom allows the synthesis of 6-O-pr opargylic ketones and electron-deficient 6-O-propargylic aromatic derivativ es by preventing intramolecular CS-enolate Michael cyclization.