Large-Scale Preparation of Pure (+)-(1S,2R,5S)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol

Abstract

A procedure is described for the preparation of (S)-(-)-pulegone, (-)-1, starting from (S)-(-)-citronellol, (-)-6, in a preparative scale. Compound (-)-1 can easily be converted into (+)-(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenylethyl) cyclohexanol: (+)-2["(+)-8-phenylmenthol"] by a procedure described in literature, which was simplified essentially. Now (+)-2 is accessible in larger amounts and thus is available as an efficient chiral auxiliary in stoichiometric asymmetric syntheses.