Diastereoselective Synthesis of 2-Cyanomethyl-3-hydroxy-5-iodomethyltetrahydrofuran from Isoxazolines by Iodoetheration

Diastereoselective 1,3-dipolar cycloaddition reaction of nitrile oxides with 1,5-hexadien-3-ol afforded syn-5-(1-hydroxy-3-butenyl)isoxazolines, which underwent iodoetheration by iodine monochloride to give 2-cyanomethyl-3-hydroxy-5-iodomethyl-tetrahydrofuran with diastereoselectivity. The relative stereochemistry of iodomethyl group varied depending on both the 3-substituents and the hydroxy protecting groups.