Total synthesis of the trifluoromethylated analog of isoaltholactone: 5-trifluoromethylisoaltholactone

The synthesis of the first fluorine-containing analog of isoaltholactone, 5-trifluoromethylisoaltholactone, was described. Key steps include nucleophilic trifluoromethylation of ketone, Horner–Wadsworth–Emmons olefination, oxidative 1,5-diol to δ-lactone conversion, diastereoselective epoxidation of olefin, and Me3SiBr-promoted deprotection/intramolecular cyclization cascade reaction.