title: Stereochemical study of a novel tautomeric furanone, homofuraneol.
abstract: 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.
authors.affiliation: 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
authors.forename: Kenji
authors.initials: K
authors.lastname: Monde
authors.forename: Atsufumi
authors.initials: A
authors.lastname: Nakahashi
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Miura
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Yaguchi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Sugimoto
authors.forename: Makoto
authors.initials: M
authors.lastname: Emura
mesh_terms: D005663:Furans / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D009812:Odorants / Q000032:analysis; D013237:Stereoisomerism
chemical_list: D005663:Furans; C029060:2-methylfuran; C113254:4-hydroxy-5-methyl-3(2H)-furanone