The 2, 3-disubstituted maleic anhydride segment of tautomycin has been synthesized in optically active form. Oxidation of 3, 4-disubstituted furan employing single oxygen completes the construction of the maleic anhydride moiety. Esterification of the maleic anhydride segment without protecting anhydride moiety resulted in the successful coupling reaction with fragment derived from tautomycin.