Enantioselective Synthesis of 2-Azido-norfuranomycin from a d-Glucose-Derived Chiral Synthon

Abstract The enantioselective synthesis of 2-azido-norfuranomycin (11) was accomplished from a d-glucose-derived chiral synthon (4). The absolute configuration at C3 and C4 of synthon 4 corresponds to that of the target molecule, confirming its utility in asymmetric synthesis. Key steps include 1,2-acetonide hydrolysis, oxidative cleavage (NaIO₄), reduction to a 2-azido-3-hydroxy olefin precursor, and ring-closing metathesis (RCM) to form the 3′,4′-dihydrofuran core. The method provides 2-azido-norfuranomycin in high yield and enantiopurity from readily available carbohydrate starting materials. A similar attempt was undertaken to obtain 2-azido-furanomycin 12.