| Oxazolidinones are a new type of synthetic antibacterial drugs with unique mechanism of action. General and concise syntheses towards novel antibacterial oxazolidinone intermediates from naturally occurring carbohydrates were developed. An efficient four-step sequence was achieved in the synthesis of homochiral 5-D-erythro-2-oxazolidinones using 2-deoxy-D-ribose as chiral synthon. Furthermore, a methodology of in situ deprotection and rearrangement of N-p-methoxybenzyl-beta-hydroxyamide to form 5-substituted-2-oxazolidinones was succeeded. An application of this methodology in the solid-state synthesis was suggested.;A template family of novel homochiral thioalkyl-substituted small ring nitrogen heterocycles was established from carbohydrate precursors. The target molecules were designed as the transition-state analogs of glycosidase inhibitors. Preliminary bio-test showed promising inhibitory activities against a gram-positive bacterial strain. |
