Preparative bioorganic chemistry, XV. Preparation of optically pure 2,4,4-trimethyl-2-cyclohexen-1-ol, a new and versatile chiral building block in terpene synthesis

Authors

  • Kenji Mori,

    Corresponding author
    1. Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan
    • Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan
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  • Prapai Puapoomchareon

    1. Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan
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Abstract

Enzymatic hydrolysis of (±)-2,4,4-trimethyl-2-cyclohexenyl acetate [(±)-3] with pig liver esterase yielded (R)-(+)-2,4,4-trimethyl-2-cyclohexen-1-ol [(R)-2] and unchanged (S)-(−)-acetate (S)-3. Enantiomerically pure (S)-2 was converted into (R)-dihydro-α-ionone (10).

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