Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides

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Abstract
Primary iodides alkylate 2-trimethylsiloxyfuran in the presence of a molar excess of silver trifluoroacetate to give the 4-alkylbut-2-en-4-olides in 55–81% yield; as an illustration of the method, the cytotoxic marine sponge constituent, 4-(methoxycarbonylmethyl)but-2-en-4-olide was prepared in 79% yield in one step.