Diastereoselective Synthesis of Methyl α-Kedarosaminide, a Carbohydrate Moiety of the Enediyne Antitumor Antibiotic Kedarcidin Chromophore

Article abstract of DOI:10.1016/0040-4039(94)85046-1

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 Me4NBH(OAc)3 for intramolecular hydride delivery.