Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides
CW Jefford, AW Sledeski, J Boukouvalas
Index: Jefford, Charles W.; Sledeski, Adam W.; Boukouvalas, John Journal of the Chemical Society, Chemical Communications, 1988 , # 5 p. 364 - 365
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Citation Number: 16
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.
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