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Synthesis 1988; 1988(10): 827-830
DOI: 10.1055/s-1988-27724
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Large-Scale Preparation of Pure (+)-(1S,2R,5S)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol

Helmut Buschmann* , Hans-Dieter Scharl
  • *Institut für Organische Chemie der RWTH Aachen, Prof.-Pirlet-Sfr.1, D-5100 Aachen, Federal Republic of Germany
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Publication Date:
12 September 2002 (online)

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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.