ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19890720625