Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 3807-3818 |
| Number of pages | 12 |
| Journal | Tetrahedron Asymmetry |
| Volume | 11 |
| Issue number | 18 |
| DOIs | |
| Publication status | Published - 2000 Sep 22 |
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Cite this
Inoue, T., Kiyota, H., & Oritani, T. (2000). 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. Tetrahedron Asymmetry, 11(18), 3807-3818. https://doi.org/10.1016/S0957-4166(00)00345-1