TOTAL SYNTHESIS OF DIMETHYL SULFOMYCINAMATE

Dimethyl sulfomycinamate (1), a methanolysis product from the natural antibiotic sulfomycin I, is synthesized in 11 steps (Scheme 19). The c hemistry of various pyridine, thiazole, and oxazole heterocycles and t heir coupling reactions under palladium catalysis are examined. The ke y transformations in the synthesis are the selective palladium-catalyz ed coupling reactions on doubly activated pyridine 62 and the condensa tion reaction between bromo ketone 69 and amide 28 to form the oxazole moiety 76. The first preparation of oxazole triflates is described, a s are some of their chemical properties.