A novel entry to cyclohexanes and cyclopentanes from carbohydrates via inversion of radical reactivity in hex-2-enono-δ-lactones

Abstract

Conjugated addition of benzenethiol, under mild conditions, to carbohydrate derived hex-2-enono-δ-lactones, substituted at C-6 or C-7 with an electron-rich insaturation, affords 3-phenylthio derivatives that, on treatment with tributyltin hydride and AIBN (azoisobutyronitrile), undergo an efficient radical cyclization to give highly functionalized cyclohexanes and cyclopentanes.