Convergent de novo synthesis of vineomycinone B2methyl ester

Abstract

An efficient de novo synthesis of vineomycinone B₂ 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 glycosylation for the construction of the aryl β-C-glycoside. A subsequent BBr₃ one-pot debenzylation, demethylation and air oxidation provided vineomycinone B₂ methyl ester.