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

…, AW Sledeski, J Boukouvalas

文献索引：Jefford, Charles W.; Sledeski, Adam W.; Boukouvalas, John Helvetica Chimica Acta, 1989 , vol. 72, p. 1362 - 1370

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被引用次数: 38

摘要

Abstract The racemic cis-and trans-5-butyltetrahydro-4-methylfuran-2-ones (= whisky lactones) and their higher homologues tetrahydro-4-methyl-5-pentylfuran-2-ones (= cognac lactones) have been prepared in 2–3 steps from 2-(trimethylsiloxy) furan. Regioselective alkylation of the latter afforded the 5-butyl-and 5-pentylfuran-2 (5H)-ones which served as precursors for the stereocontrolled construction of either diastereoisomer of the beverage ...