A formal synthesis of the syributins and secosyrins and a synthetic approach toward the syringolides

Article abstract of DOI:10.1016/S0040-4039(98)01944-3

The indium-mediated allylation of a protected derivative of D-xylulose in aqueous THF is highly diastereoselective. The obtained product has been converted in four steps into a spiro lactone previously transformed into syributins and secosyrins. This remarkably short reaction sequence constitutes therefore a formal synthesis of these compounds and provides also a promising synthetic approach towards the syringolides.