Taking control of P1, P1' and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics.
A protocol for the stereocontrolled independent preparation of both C-2 epimers of Phe-Phe trans-vinyl amide isostere dipeptidomimetics has been devised based on a Wittig-type reaction, in which two chiral building blocks were joined with excellent E-selectivity to give compounds of the type PhePsi[(E)-CH[double bond, length as m-dash]CH]-PheOH.
Wiktelius
Daniel
D
Department of Chemistry, Medicinal Chemistry, Göteborg University, SE-412 96, Göteborg, Sweden.
Luthman
Kristina
K
D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000475:Alkenes; D000577:Amides; D001555:Benzene Derivatives; D004151:Dipeptides