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Synthesis 1990; 1990(11): 1053-1056
DOI: 10.1055/s-1990-27091
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Synthesis of Tercyclohexanones

Eldon G. Nidy* , David R. Graber, Paul A. Spinelli, John C. Sih, Roy A. Johnson
  • *The Upjohn Company, Pharmaceutical Research and Development, Kalamazoo, Michigan, MI 49001, USA
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Publication Date:
17 September 2002 (online)

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A synthetic route to tercyclohexanones is described in which alkylation of 4-cyclohexylcyclohexanone with the dianion of 4,4-(ethylenedioxy)cyclohexanecarboxylic acid gives 1-carboxy-1′-hydroxyl-1,1′:4′,1″-tercyclohexan-4-one ethylene ketal. Decarboxylative dehydration of the latter followed by hydrolysis of the ketal gives 4-(4′-cyclohexylcyclohexylidene)cyclohexanone. Hydrogenation of this compound gives cis- and trans-1,1′:4′,1″-tecyclohexan-4-one, the latter of which is correlated with authentic trans-1,1′:4′,1″-tercyclohexane.