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.