The synthesis of lincomycin

Abstract

Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside(16), the intact carbohydrate portion of the antibiotic lincomycin (1), has been synthesised from D-galactose. The amino-alcohol side chain was attached to 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdopyranose-(1,5)(2) by two independent procedures, and the glycosidic thiomethyl group was introduced in the final stages of the synthesis. This work completes the requirements for the total chemical synthesis of the antibiotic.