Cycloaddition reactions of carbohydrate derivatives. Part IV. Synthesis of a tetrahydroxyindolizidine through a cyclic nitrone prepared from D-xylose

Article abstract of DOI:10.1016/S0040-4039(00)77531-9

Intramolecular conjugate addition of the oxime from aldehyde 5 led to the formation of cyclic nitrone 6. 1,3-Dipolar cycloaddition of the latter with methyl acrylate gave the bicyclic 7 with high diastereoselection. Subsequent four-step transformation of