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.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM035557-02
Application #
3288512
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1985-06-01
Project End
1988-05-31
Budget Start
1986-06-01
Budget End
1987-05-31
Support Year
2
Fiscal Year
1986
Total Cost
Indirect Cost
Name
Case Western Reserve University
Department
Type
DUNS #
077758407
City
Cleveland
State
OH
Country
United States
Zip Code
44106