18688-70-5Relevant articles and documents
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
, p. 1362 - 1370 (2007/10/02)
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.
