The purpose of this study is to develop a general synthetic approach to a class of aminosugar antibiotics which include furanomycin, polyoxin J, miharamycin B, and lincomycin. The unifying structural feature of these compounds consists of either an erythro or threo disposed vicinal amino alkoxide moiety. Methodology will be explored which allows for the construction of such systems in chiral form with emphasis on acyclic stereocontrol. Towards this end, the use of chelation-controlled additions to chiral aldehydes and 1,3-dipolar cycloadditions involving a chiral nitrone will be investigated. The stereochemical course of these processes may be ascertained using high field NMR spectroscopy and/or chemical correlation with known systems. Should our predictions hold true, these results would be applicable to variety of synthetic endeavors. Thus, we hope to address the synthetic problems associated with these systems and apply the results to the preparation of medicinally and agriculturally useful natural products.
