Scientific article

Synthesis of cis and trans Whisky and Cognac Lactones by the Regiocontrolled Alkylation of 2-(Trimethylsiloxy)furan

Published inHelvetica Chimica Acta, vol. 72, no. 6, p. 1362-1370
Publication date1989

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 lactones. The structure and tautomerization of the diazomethane adducts of these 5-alkylfuran-2(5H)-ones are also described.

  • Swiss National Science Foundation - 2.632-0.87
Citation (ISO format)
JEFFORD, Charles, SLEDESKI, Wojciech Adam, BOUKOUVALAS, John. Synthesis of <i>cis</i> and <i>trans</i> Whisky and Cognac Lactones by the Regiocontrolled Alkylation of 2-(Trimethylsiloxy)furan. In: Helvetica Chimica Acta, 1989, vol. 72, n° 6, p. 1362–1370. doi: 10.1002/hlca.19890720625
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Article (Published version)
ISSN of the journal0018-019X

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