Syntheses of 3- O-substituted 3- O-demethylsporaricins A

Abstract

The 3- O-methyl group of sporaricin A has been replaced by other alkyl groups to give 3- O-(3-amino-2-hydroxypropyl)- ( 13), 3- O-(4-amino-2-hydroxybutyl)- ( 15), and 3- O-(2,3-dihydroxypropyl)-sporaricin A ( 14). The 3- O-methyl group of sporaricin B was selectively removed under acidic conditions, and an allyl group was introduced onto the 3-hydroxyl group. The 3- O-allyl compound was 4- N-glycylated, the allyl group epoxidized, and the product treated with sodium azide or potassium cyanide, or hydrolyzed. The respective derivative obtained was then reduced, or deprotected, or both, to give 13, 15, and 14. These compounds showed high antibacterial activities against bacteria resistant to sporaricin A.