Total Synthesis of (+)‐Awajanomycin

Abstract

Abstract The total synthesis of (+)‐awajanomycin has been achieved by asymmetric allylboration of a vicinal tricarbonyl compound as the key step. A substrate‐controlled dihydroxylation and subsequent differentiation of diastereotopic ester groups were used to synthesize the γ‐lactone substructure. After formation of the δ‐lactam, the bicyclic core structure was established. The synthetic strategy and overall efficacy is compared with Huang's route to awajanomycin.