Tetrahedron Asymmetry p. 3807 - 3818 (2000)
Update date:2022-08-05
Topics: Purification Resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid Conversion of (R)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid to cis-α-irone Conversion of (S)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid to cis-γ-irone
Inoue, Takahiro
Kiyota, Hiromasa
Oritani, Takayuki
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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Doi:10.1007/BF00862213
()Doi:10.1021/om000143u
(2000)Doi:10.1055/s-2000-8719
(2000)Doi:10.1021/ol0003533
(2001)Doi:10.1055/s-2000-8712
(2000)Doi:10.1007/BF00480718
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