合成路线1

Aryl lithium reagent (II) (prepared by halogen-metal exchange of 1-chloro-4-iodobenzene (I) with tert-butyllithium at -60 C), was added to 1,4-cyclohexanedione mono-ethylene ketal (III) to yield tertiary alcohol (IV). Then, mild acid hydrolysis of (IV) with pyridinium tosylate in aqueous acetone provided ketone (V). Deoxygenation of the benzylic alcohol of (V) with P2I4 in refluxing benzene produced the arylcyclohexanone (VI), which was further reduced to the trans cyclohexanol (VII) with NaBH4 in MeOH. Subsequent acylation of (VIII) with oxalyl chloride, followed by an aqueous quench furnished the oxalic acid monoester (VIII). The free-radical decarboxylative coupling of (VIII) with 2-chloronaphthoquinone (IX), promoted by ammonium persulfate and a trace of AgNO3 under phase-transfer conditions, provided the desired cyclohexylquinone (X) together with the cyclohexyl ester (XI) as mixtures of cis and trans isomers, which were separated by flash chromatography. Finally, conversion of the trans-(X) to the target hydroxylated compound was performed by treatment with KOH in boiling MeOH.