Summary
Under the influence of sodium amide, caryophyllenic acid dimethylester undergoes an initial splitting which may be regarded as a reversed Michael-reaction. The intermediate then undergoes a cyclization to give an unsaturatedβ-keto-ester. The latter has been transformed by well-defined reactions into 4,4-dimethyl-cyclohexanone. This result is a further proof that, of the two possible structural formulas (I) and (II) for caryophyllenic acid, formula (I) is the correct one.
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Eschenmoser, A., Fürst, A. Zur Konstitution der Caryophyllensäure. Experientia 7, 290–291 (1951). https://doi.org/10.1007/BF02150543
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DOI: https://doi.org/10.1007/BF02150543