3′and 4′ and equatorial amino and hydroxy derivatives of neamine

Abstract

All eight of the possible amino and hydroxyl derivatives at the 3′ and 4′ positions of neamine were prepared. The compounds are either 3′-deoxy or 4′-deoxy analogs having axial or equatorial amino or hydroxyl groups at the other position. The position and configuration of the hydroxyl groups from the reduction of the two 3′, 4′-epoxides, 11 and 12, were established. The 3′-keto and 4′-keto derivatives ( 26 and 23) and also the corresponding oximino acetates, 33b and 35b, were reduced and the structures of the products determined. Hydrolytic cleavage of the exo-methylene epoxides at the 3′ and 4′ positions gave the diols, 47 and 45. N.m.r. data for the 3′ and 4′ acetates and acetamides are presented.