;Abstract In this paper, ethyl L-lactate was used as a starting material to synthesize Z-type and E-type alkenes (6 E、16 Z、24 Z) through a multi-step reaction, respectively. The compounds synthesize 4-methyl-3-oxa-1-azabicyclo[3.1.0] hexan-2-one (11、19、27), followed by a 4-methyl-3-oxa-1-azabicyclo[3.1.0] hexan-2-one is subjected to a nucleophilic addition reaction with a nucleophile to form a single diastereoisomer to construct a chiral quaternary carbon center. Finally, the method of constructing a chiral quaternary carbon center was applied to ent-D-Kijanose′s synthesis strategy. Since D-Kijanose is a branched nitrosuga, which connects with the biologically active Kijanimicin, it has antitumor and antibiotic activity.Therefore, the synthesis of ent-Kijanoside is the target product of this paper. Keywords: aziridine, chiral quaternary carbon center, diastereoselectivity, ent-Kijanoside.
