6-EXO FREE-RADICAL CYCLIZATION OF ACYCLIC CARBOHYDRATE INTERMEDIATES - A NEW SYNTHETIC ROUTE TO ENANTIOMERICALLY PURE POLYHYDROXYLATED CYCLOHEXANE DERIVATIVES

The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.