Stereoselective synthesis of substituted piperidines - Total synthesis andabsolute configurations of (+)- and (-)-dienomycin C

The first total asymmetric synthesis and the attribution of the absolute co nfigurations of (+)-dienomycin C (1), an alkaloid isolated from a Streptomy ces strain, are reported. This compound was prepared in six steps from the enantiopure tricarbonyl(dienal)iron complex (+)-4 which is easily obtained by separating preformed diastereomers, starting from phenylpentadienoic aci d and (S)-methyl mandelate.