Deoxygenation of Amino-Glycoside Antibiotics via Anhydro Intermediates. III. New Synthesis of 3'-Deoxykanamycin A

Abstract

A new synthetic route has been exploited for the large-scale production of 3'-deoxykanamycin A. The key stage in the synthesis involves the formation of the 3', 4'-anhydro-3'-epi derivative (9) or 2', 3'-anhydro-3'-epi derivative (10) followed by conversion to the 3'-deoxy derivative by reduction with Raney-nickel or sodium borohydride. Compound (9) or (10) was prepared by the treatment of 2', 2"-di-O-benzoyl-3'-O-methylsulfonyl-tetra-N-ethoxycarbonylkanamycin A with sodium methoxide.