Synthesis of Oxidized Spiroketals via 2-Furyl Ketone Oxidation-Rearrangement

Article abstract of DOI:10.1021/jo00270a010

A new method for the synthesis of highly oxidized spiroketals has been developed via the oxidation-rearrangement of 2-furyl ketones, readily available by the reaction of furyllithium reagents with lactones.Spiroketals hydroxylated in the 2-position are produced as slowly equilibrating mixtures of diastereomers in good yield.The method has been applied to the synthesis of trioxadispiroketals modeling those present in the polyether antibiotics salinomycin, narasin, and their analogues.