Diastereoselective synthesis of methyl α-kedarosaminide, a carbohydrate moiety of the enediyne antitumor antibiotic kedarcidin chromophore

Abstract

Methyl α-kedarosaminide ( 9), a carbohydrate moiety of the enediyne antitumor antibiotic kedarcidin chromophore, was synthesised from d-threonine. Stereoselective reduction of the allyl ketone 5 derived from d-threonine was a key step in the synthesis, which was achieved by using Me 4NBH(OAc) 3 for intramolecular hydride delivery.