Application of intramolecular 1,3-dipolar nitrone cycloaddition reaction on carbohydrate-derived precursors containing an olefin functionality at C-1 or C-3 or C-5 and a nitrone moiety at C-2 or C-3 as appropriate has resulted in the formation of structurally new cycloaddition products containing furanose-fused oxepane, thiepane, azepane, cyclopentane, cycloheptane, tetrahydrofuran, and pyranose-fused tetrahydrofuran rings. The structure and stereochemistry of these products have been characterized by spectral as well as single-crystal X-ray analyses. Two of the compounds have been transformed to the bicyclic nucleoside derivatives applying Vorbrüggen reaction conditions.
Protocol. -The preparation of the target system (V), which is required for DNA studies, involves initial deprotonation of substrates (III) by basic alumina, trapping of the resulting 1,3-dipole with acetylenic esters and subsequent aromatization. -(PAIRA, R.; MONDAL, S.; CHOWDHURY, A.; BANERJEE, M.; MAITY, A.; HAZRA, A.; MONDAL*, N. B.; Tetrahedron Lett. 54 (2013) 24, 3046-3050, http://dx.
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