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Three stereoisomeric inhibitors of Pin1: (2 R ,5 S )-, (2 S ,5 R )- and (2 S ,5 S )-Ac–pSer–Ψ[( Z )CH = C]–pipecolyl(Pip)–2-(2-naphthyl)ethylamine  1 , that mimic L-pSer–D-Pro, D-pSer–L-Pro, and D-pSer–D-Pro amides respectively, were synthesized by a 13-step route. The newly formed stereogenic centers in the pipecolyl ring were introduced by Luche reduction, followed by stereospecific [ 2 , 3 ]-Still-Wittig rearrangement. The ( Z )- to ( E )-alkene ratio in the rearrangements were consistently 5.5 to 1. The stereochemistry at the original Ser α-carbon controlled the stereochemistry of the Luche reduction, but it did not affect the stereochemical outcome of the rearrangement, which consistently gave the ( Z )-alkene. The epimerized by-product,  (2 S ,5 S )-10 , resulting from the work-up after Na/NH 3  debenzylation of  (2 S ,5 R )-9 , was carried on to the  (2 S ,5 S )-1  isomer. Compound  (2 S ,5 S )-10  was resynthesized from the Luche reduction by-product,  (2 R ,3 R )-3 , and the stereochemistry was confirmed by comparison of the optical rotations. The IC 50  values for  (2 R ,5 S )-1 ,  (2 S ,5 R )-1  and  (2 S ,5 S )-1  Pin1 inhibition were: 52, 85, and 140 μM, respectively.

Stereochemical Control in the Still-Wittig Rearrangement Synthesis of Cyclohexyl (Z)-Alkene Inhibitors of Pin1