Convergent de novo synthesis of vineomycinone B_2 methyl ester

摘要

An efficient de novo synthesis of vineomycinone B_2 methyl ester has been achieved. The longest linear route required only 14 steps from achiral commercially available starting materials (4.0% overall yield). The key transformations included the de novo asymmetric synthesis of two key fragments, which were joined by a convergent late stage Suzuki's gtycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr_3 one-pot debenzylation, demethylation and air oxidation provided vineomycinone B_2 methyl ester.