en
Scientific article
English

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

Funding
  • 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
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0018-019X
135views
0downloads

Technical informations

Creation07/08/2021 4:04:00 PM
First validation07/08/2021 4:04:00 PM
Update time03/16/2023 12:52:31 AM
Status update03/16/2023 12:52:31 AM
Last indexation01/17/2024 1:40:07 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack