ORGN 13 |
New synthetic routes to chiral cyclic carbamates from carbohydrate derivatives
| Guijun Wang, Vibha Sharma, and Jean Rene Ella-Menye. Department of Chemistry, University of New Orleans, 2000 Lake shore drive, New Orleans, LA 70148 |
| Chiral cyclic carbamates are important building blocks for the synthesis of many pharmaceutical compounds and intermediates in the synthesis of chiral amino alcohols. The 5-hydroxymethyl 2-oxazolidinones (I) or 5-aminomethyl 2-oxazolidinones (II) are important core structures in several classes of biologically active compounds. These include antibiotics and agents for neurological disorder. The homologous cyclic carbamate tetrahydro oxazinones (III) are also useful intermediates in synthesizing natural products and amino alcohols. The oxazinanone derivatives are being explored as drugs for inflammatory disease, ulcer, allergy and arthritis. The chiral versions of these cyclic carbamates are difficult to synthesize. Several new approaches using carbohydrate derivative S-3-hydroxy gamma butyrolactone to the synthesis of these molecules will be discussed in the paper. 
|
| |
|
|