The first total syntheses of(+)-trienomycins A and F, representative members of a new class of cytotoxic ansamycin antibiotics, have been achieved. Key features of the unified synthetic scheme included incorporation of the (E,E,E)-triene unit with concomitant macrocyclization via a novel bis-Wittig olefination and the use of (2,2,2-trichloroethoxy)methyl protecting group for the secondary amide.