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Mercury(II)-mediated routes to some side-chain functionalised 1,7-dioxaspiro[5.5]undecanes. Applications of Luche-Barbier chemoselective addition to ketoaldehydes

The ketoaldehyde, 5-oxo-9-decenal (4) undergoes chemoselective addition to the aldehyde with either allyl or propargyl bromide under Luche-Barbier conditions. Oxymercuration-cyclisation of the resulting hydroxyketones, followed by reductive or oxidative demercuration, provides functionalised spiroacetals, some of which are of insect origin