Total synthesis of (+)-nojirimycin and (+)-1-deoxynojirimycin

H Iida, N Yamazaki, C Kibayashi

Index: Iida, Hideo; Yamazaki, Naoki; Kibayashi, Chihiro Journal of Organic Chemistry, 1987 ,  vol. 52,  # 15  p. 3337 - 3342

Full Text: HTML

Citation Number: 135

Abstract

An efficient chiral total 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, 3-0-isopropylidene-~-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 ...