The total synthesis of butirosin B (5) is described. Its 3′,4′-dideoxy derivative (11) has been synthesized, a cyclic carbamate derivative (2) being used as the key compound. The dideoxy derivative (11) was prepared by hydrogenation of a 3′,4′-unsaturated derivative (10) obtained by the reaction of a di-O-mesyl derivative (9) with sodium iodide and zinc dust. The dideoxy derivative (11) was found to have significant activity against resistant bacteria producing phosphotransferase I.
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Ikeda et al. (1974) studied this question.