Selected regiocontrolled transformations applied to the synthesis of (1S)-cis-chrysanthemic acid from (1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol.
(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.
Krief
Alain
A
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
Gondal
Humaira Y
HY
Kremer
Adrian
A
D003511:Cyclohexanols / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011722:Pyrethrins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C533583:(1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol; D003511:Cyclohexanols; D004852:Epoxy Compounds; D011722:Pyrethrins; C007051:chrysanthemic acid