Tetrahedron

Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1, 4-dideoxy-1, 4-imino-D-lyxitol; L-deoxymannojirimycin; rhammo-1-deoxynojirimycin and 1- …

…, CJ Andres, JE Resek, CC Woodall, MA McLaughlin…

Index: Meyers; Andres, Charles J.; Resek, James E.; Woodall, Charlotte C.; McLaughlin, Maureen A.; Lee, Peter H.; Price, David A. Tetrahedron, 1999 , vol. 55, # 29 p. 8931 - 8952

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Citation Number: 71

Abstract

By employing the appropriate chiral bicyclic lactams, the asymmetric total synthesis of four enantiopure azasugars mentioned in the title were successfully achieved. A series of diastereoselective oxidations (OsO 4NMO) followed by diastereoselective reductions (BH3, 9-BBN) gave good yields of the trisubstituted (16) and tetrasubstituted (2, 3, 4) pyrrolidine and piperidines respectively.