SYNTHESIS OF AMINOTRIDEOXYBUTIROSIN A, A CHEMICALLY MODIFIED ANTIBIOTIC ACTIVE AGAINST BUTIROSIN-RESISTANT BACTERIA

Abstract

5"-Amino-3', 4', 5"-trideoxybutirosin A (4) was synthesized by two routes starting from the known tri-O-acetyl-tetra-N-benzyloxycarbonyl-3", 5"-O-cyclohexylidene-3', 4'-di-O-mesylbutirosin A (5). Introduction of amino function at C-5" was carried out by displacement of 5"-tosyloxy group with sodium azide either before or after 3', 4'-deoxygenation. Compound 4 shows outstanding activities against strains including Pseudomonas aeruginosa and Escherichia coli which are highly resistant to butirosin and 5"-amino-5"-deoxybutirosin A (2).