Total Synthesis of Lajollamycin B

Abstract The first total synthesis of lajollamycin B, a structurally novel nitro‐tetraene spiro‐β‐lactone/γ‐lactone antibiotic, is described. The convergent synthesis involves the construction of the C8′–C11′ nitrodienylstannane and its coupling with the segment prepared from the C1′–C7′ ω‐iodoheptadienoic acid and the right‐hand heterocyclic fragment, which has been utilized for our previous syntheses of oxazolomycin A. The revision of the geometry of the terminal Δ10′, 11′‐double bond from E to Z is also described for the structure of natural lajollamycin B.