Selected regiocontrolled transformations applied to the synthesis of (1S)-cis-chrysanthemic acid from (1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol

Alain Krief; Humaira Y Gondal; Adrian Kremer

doi:10.1039/b808695h

Selected regiocontrolled transformations applied to the synthesis of (1S)-cis-chrysanthemic acid from (1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol

Chem Commun (Camb). 2008 Oct 21:(39):4753-5. doi: 10.1039/b808695h. Epub 2008 Aug 26.

Authors

Alain Krief¹, Humaira Y Gondal, Adrian Kremer

Affiliation

¹ Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, 5000, Namur, Belgium. alain.krief@fundp.ac.be

PMID: 18830482
DOI: 10.1039/b808695h

Abstract

(1S)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry using regiocontrolled epoxide ring opening, diol mono-oxidation and cyclopropanation.

MeSH terms

Cyclohexanols / chemistry*
Epoxy Compounds / chemistry*
Molecular Structure
Pyrethrins / chemical synthesis*
Pyrethrins / chemistry
Stereoisomerism

Substances

(1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol
Cyclohexanols
Epoxy Compounds
Pyrethrins
chrysanthemic acid