Synthetic studies on nucleoside-type muraymycins antibiotics based on the use of sulfur ylides. Synthesis of bioactive 5′-epimuraymycin analogues

A new synthetic approach to the 5-epimers of muraymycins, a family of complex nucleoside-type antibiotics, is reported based on the synthesis of epoxy amides obtained via the reaction of sulfur ylides with the uridyl aldehyde derivatives , and , followed by a subsequent oxirane ring opening reaction with diamines. This new strategy offers an excellent opportunity for the preparation of muraymycin analogues of biological interest. In fact, biological studies have revealed these 5′-epimers to be as biologically potent as the natural antibiotics, aside of representing a convergent and flexible route towards the natural congeners.