Total Synthesis of (+)-Nojirimycin and (+)-1-Deoxynojirimycin

Article abstract of DOI:10.1021/jo00391a031

An efficient chiral synthesis of (+)-nojirimycin (1) and (+)-1-deoxynojirimycin (2) has been achieved in optically pure form via the common intermediate 11 derived from the nonsugar chiral pool.The monosilyl derivative 4 of 2,3-O-isopropylidene-L-threitol (3) was converted to the (E)-allyl alcohol 8, which upon asymmetric epoxidation provided the syn epoxide 9.Regio- and stereoselective epoxide opening reaction of 9 followed by methoxymethylation yielded the azide 11, which afforded in five steps (+)-1-deoxynojirimycin (2).The azide 11 could also serve as the intermediate for the synthesis of (+)-nojirimycin (1), which was thus derived from 11 in six steps.