Synthesis of chiral, densely functionalized medium-sized rings from carbohydrate precursors via regioselective exo/endo-primary alkyl radical cyclizations

The first 8-endo-trig and 7-exo-dig carbocyclizations of primary alkyl free radicals on acyclic carbohydrate templates derived from d-glucose, leading to chiral and polyfunctionalized medium-sized carbocycles are described.