%A EM Skoda
%A GC Davis
%A P Wipf
%J Organic Process Research and Development
%T Allylic amines as key building blocks in the synthesis of (E)-alkene peptide isosteres
%X Nucleophilic imine additions with vinyl organometallics have developed into efficient, high-yielding, and robust methodologies to generate structurally diverse allylic amines. We have used the hydrozirconation/transmetalation/imine addition protocol in the synthesis of allylic amine intermediates for peptide bond isosteres, phosphatase inhibitors, and mitochondria-targeted peptide mimetics. The gramicidin S-derived XJB-5-131 and JP4-039 and their analogues have been prepared on up to 160-g scale for preclinical studies. These (E)-alkene peptide isosteres adopt type II ?-turn secondary structures and display impressive biological properties including selective reactions with reactive oxygen species (ROS) and prevention of apoptosis. ? 2012 American Chemical Society.
%N 1
%P 26 - 34
%V 16
%D 2012
%R 10.1021/op2002613
%L pittir18732