Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals.

The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-Bu)2(o-biphenyl)]Cl and AgOTf is employed in THF at 0 °C. A range of differentially substituted triols leading to substituted 5- and 6-membered ring spiroketals were prepared and function well in the reaction.