1,3-dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: Synthesis of 2-hydroxy-1-deoxycastanospermine analogues

The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine and 2-hydroxyl-1-deoxy-8a-epi-castano-spermine is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to D-glucose derived nitrone, followed by tosylation that afforded four diastereomeric sugar-substituted isoxazolidines with the desired regioselectivity.