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

Three stereoisomeric inhibitors of Pin1: (2R,5S)-, (2S,5R)- and (2S,5S)-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 pipeco...

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Publicat a:PLoS One
Autors principals: Chen, Xingguo R., Fan, Shuang A., Ware, Rachel I., Etzkorn, Felicia A.
Format: Artigo
Idioma:Inglês
Publicat: Public Library of Science 2015
Matèries:
Accés en línia:https://ncbi.nlm.nih.gov/pmc/articles/PMC4596862/
https://ncbi.nlm.nih.gov/pubmed/26445009
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1371/journal.pone.0139543
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