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

Full Text: HTML

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.

Related Articles:

Synthesis of cis and trans Whisky and Cognac lactones by the regiocontrolled alkylation of 2??(trimethylsiloxy) furan

[Jefford, Charles W.; Sledeski, Adam W.; Boukouvalas, John Helvetica Chimica Acta, 1989 , vol. 72, p. 1362 - 1370]

Syntheses of dialkyl and functionalized ketones via 1-(benzotriazol-1-yl) alkyl methyl thioethers

[Katritzky, Alan R.; Oniciu, Daniela C.; Ghiviriga, Ion; Soti, Ferenc Journal of Organic Chemistry, 1998 , vol. 63, # 7 p. 2110 - 2115]

Synthesis of cis and trans Whisky and Cognac lactones by the regiocontrolled alkylation of 2??(trimethylsiloxy) furan

[Jefford, Charles W.; Sledeski, Adam W.; Boukouvalas, John Helvetica Chimica Acta, 1989 , vol. 72, p. 1362 - 1370]

Synthesis of cis and trans Whisky and Cognac lactones by the regiocontrolled alkylation of 2??(trimethylsiloxy) furan

[Jefford, Charles W.; Sledeski, Adam W.; Boukouvalas, John Helvetica Chimica Acta, 1989 , vol. 72, p. 1362 - 1370]

Synthesis of cis and trans Whisky and Cognac lactones by the regiocontrolled alkylation of 2??(trimethylsiloxy) furan

[Jefford, Charles W.; Sledeski, Adam W.; Boukouvalas, John Helvetica Chimica Acta, 1989 , vol. 72, p. 1362 - 1370]

More Articles...