Collect. Czech. Chem. Commun. 1986, 51, 1316-1322

Synthesis of some monoterpenols via cyclopropylcarbinyl rearrangement

Alexander M. Moiseenkov and Boris A. Czeskis

N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences, Moscow, U>S>S>R>


Condensation of appropriately substituted aldehydes and Grignard reagents leads to cyclopropyl alcohols V - VIII chromatographically separated in all cases into individual diastereoisomers. Perchloric acid catalyzed cyclopropylcarbinyl rearrangement of V - VIII (as a mixture of diastereoisomers or individual isomers) gives unsaturated monoterpenols IX - XII with high regio- and stereospecifity.