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Stereoselective synthesis of cis-p-menth-8-ene-1,7-diol, cis-p-menthane-1,7-diol, and cis-p-menthane-1,7,8-triol.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2005 Apr 22; Vol. 11 (9), pp. 2783-7. - Publication Year :
- 2005
-
Abstract
- The natural products cis-p-menthane-1,7-diol (cis-IV), cis-p-menth-8-ene-1,7-diol (cis-I) and cis-p-menthane-1,7,8-triol (cis-II) are obtained starting from the corresponding cis-cyanohydrins, cis-2 and cis-7, respectively, by chemical transformation of the cyano into the hydroxymethyl group. The key step of the synthesis is the very high cis-selectivity (> or = 96 %) of the MeHNL-catalyzed HCN addition to 4-alkylcyclohexanones. From 4-isopropylcyclohexanone (1) the cyanohydrin cis-2 and from 4-(1-methylvinyl)cyclohexanone (6) the cyanohydrin cis-7 result almost quantitatively. Regioselective hydroxylation of cis-I affords the triol cis-II. X-ray crystal structure determinations of the final products confirm their cis-configuration.
- Subjects :
- Crystallography, X-Ray
Cyclohexane Monoterpenes
Hydrogen Cyanide chemistry
Menthol chemical synthesis
Menthol chemistry
Molecular Structure
Monoterpenes chemistry
Nuclear Magnetic Resonance, Biomolecular
Stereoisomerism
Menthol analogs & derivatives
Monoterpenes chemical synthesis
Nitriles chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 0947-6539
- Volume :
- 11
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 15736149
- Full Text :
- https://doi.org/10.1002/chem.200401147