Asymmetric synthesis of novel polyhydroxylated derivatives of indolizidine and quinolizidine by intramolecular 1,3-dipolar cycloaddition of N-(3-alkenyl)nitrones

Abstract

Reaction of 3-O-benzyl-1,2-O-isopropylidene-1,5-pentadialdo-α- D-xylofuranose with N-(1,1-dimethylbut-3-enyl)hydroxylamine followed by intramolecular 1,3-dipolar cycloaddition yields 7-oxa-1-azabicyclo[2.2.1]heptane derivative 4, which is easily converted into novel polyhydroxylated quinolizidine 6 and indolizidine 8.