An approach to the cyclohexyl moiety of the immunosuppressive agent FK-506

Abstract

Tricarbonyl(3-methoxycyclohexadienyl)iron hexafluorophosphate, which is readily prepared from 1,3-dimethoxybenzene, was treated with the enolate of methyl phenylsulphonylacetate to give an adduct which was decarboxylated and decomplexed to give 5-phenylsulphonylmethylcyclohexenone. This compound was converted by a four-step, highly stereoselective, sequence to the trisubstituted cyclohexane (2), which represents a cyclohexyl moiety building block for FK-506.