Modifications of lincomycin involving the carbohydrate portion. Part III. The 7-O-methyl and 6-de-(1-hydroxyethyl) analogues

Abstract

7-O-Methyl-lincomycin has been synthesised, by use as intermediates of the carbohydrate portions of both the antibiotics lincomycin and celesticetin. The use of the latter involved the development of a method for introducing the axial glycosidic methylthio-substituent, and this method permitted the synthesis of 6-de-(1-hydroxyethyl)lincomycin from D-galactose. The 7-O-methyl analogue possesses enhanced antibacterial activity, whereas the analogue lacking C-7 and C-8 shows 1% of the antibacterial activity of the parent in in vitro tests.