Abstract
2,6-Anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-d-gluco-hept-1-enitol (3) was converted into allyl 3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-α-d-gluco-2-heptulopyranoside (4) upon addition of allylic alcohol in the presence of N-iodosuccinimide. Treatment of 4 with tributylin hydride triggered as a stereolselective exo-Dig radical cyclisation, opening a novel route to the synthesis of the 1,6-dioxaspiro[4.5]decane ring system.
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