Abstract
Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.
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