Free radical reactions of carbohydrate derivatives in the synthesis of carbocyclic compounds. 1. Intramolecular C2–C6 cyclization of monosaccharides — A new route to substituted cyclopentanes

The feasibility of adopting a new approach to the preparation of chiral carbocyclic compounds has been demonstrated by experiment. Synthesis was achieved by way of intramolecular free radical C₂–C₆ cyclization of carbohydrate derivatives, which produced compounds with quaternary C₂ carbon atom having a strictly defined configuration.N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117334 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 650–657, March, 1992.