抄録
Dysiherbaine, a glutamic acid derivative bearing an amino-sugar moiety, exhibits strong non-NMDA-glutamate receptor agonist activity. In this study, the amino sugar moiety of dysiherbaine was synthesized by using addition reaction to a nitrone with 2-trimethylsilyloxyfuran. The starting nitrone was readily prepared from 2,3-isopropylidene-D-glyceraldehyde and 2,3:5,6-O-diisopropylidene-L-gulofuranose oxime. The nitrone, on treatment with 2-trimethylsilyloxyfuran in the presence of a catalytic amount of TMSOTf at –78 °C, underwent nucleophilic addition reaction to give bicyclic adduct as a single stereoisomer after work-up with TBAF. The bicyclic adduct was elaborated to the key synthetic intermediate having a protected amino-sugar moiety of dysiherbaine in 11 steps which involved reductive N-methylation, sequential reductive N–O bond-cleavage and formation of oxazolidinone ring.
