TY - JOUR
T1 - Synthesis of both enantiomers of cis-α-irone and cis-γ-irone, principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid
AU - Inoue, Takahiro
AU - Kiyota, Hiromasa
AU - Oritani, Takayuki
PY - 2000/9/22
Y1 - 2000/9/22
N2 - The principal constituents of iris oil, (-)-cis-α-irone and (-)-cis-γ-irone, and their enantiomers, were synthesized from (-)- and (+)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acids. The racemic acid was resolved by recrystallization of its salt with a chiral amine, or by enzymatic hydrolysis of the corresponding alcohol. The fragrances of (-)-(1R,5S)-cis-α-irone and (-)-(1R,5S)-cis-γ-irone were superior to those of (+)-(1S,5R)-cis-α-irone and (+)-(1S,5R)-cis-γ-irone. Copyright (C) 2000 Elsevier Science Ltd.
AB - The principal constituents of iris oil, (-)-cis-α-irone and (-)-cis-γ-irone, and their enantiomers, were synthesized from (-)- and (+)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acids. The racemic acid was resolved by recrystallization of its salt with a chiral amine, or by enzymatic hydrolysis of the corresponding alcohol. The fragrances of (-)-(1R,5S)-cis-α-irone and (-)-(1R,5S)-cis-γ-irone were superior to those of (+)-(1S,5R)-cis-α-irone and (+)-(1S,5R)-cis-γ-irone. Copyright (C) 2000 Elsevier Science Ltd.
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U2 - 10.1016/S0957-4166(00)00345-1
DO - 10.1016/S0957-4166(00)00345-1
M3 - Article
AN - SCOPUS:0034703163
VL - 11
SP - 3807
EP - 3818
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 18
ER -