Stereochemical study of a novel tautomeric furanone, homofuraneol.
A mixture of tautomers with unique keto-enol structures, 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one and 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one (EHMF, homofuraneol, 1a and 1b), comprises four structural isomers including their enantiomers. The four isomers were successfully separated by chromatographic optical resolution, and their odor evaluation was performed. Determination of the absolute chemistry of 1a and 1b were accomplished for the first time by direct measurement of the VCD spectra of their methyl ether derivatives 4a and 4b compared with the calculated ones as well as chemical relay reaction. The relationship between odor characteristics and stereochemistry was also examined.
Monde
Kenji
K
Faculty of Advanced Life Science, Frontier Research Center for the Post-Genome Science and Technology, Hokkaido University, Sapporo, Japan. kmonde@glyco.sci.hokudai.ac.jp
Nakahashi
Atsufumi
A
Miura
Nobuaki
N
Yaguchi
Yoshihiro
Y
Sugimoto
Daisuke
D
Emura
Makoto
M
D005663:Furans / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D009812:Odorants / Q000032:analysis; D013237:Stereoisomerism
D005663:Furans; C029060:2-methylfuran; C113254:4-hydroxy-5-methyl-3(2H)-furanone