Carbocycles from Carbohydrates via Free Radical Cyclizations: Synthesis and Manipulation of Annulated Furanoses

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Abstract
Tributyltin hydride plus AIBN mediated free radical cyclization of chiral precursors derived from O-glycosylated carbohydrates is an efficient method for the asymmetric synthesis of carbocycles (cyclitols, aminocyclitols and pseudosugars) of biological and pharmacological interest. Starting from simple aldoses and after a series of trivial synthetic steps for hydroxyl protection and functionalization, it is possible to prepare the required radical precursor in the furanose form with a radical donor and acceptor at the appropriate positions. Under typical free radical cyclization conditions the desired annulated furanoses were obtained in good chemical yield and excellent acyclic diastereoselection at "off-template" sites. A large number of precursors have been synthesized and cyclized in order to analyze the scope and extent of this new synthetic methodology.

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