642073-53-8Relevant articles and documents
Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A
Berthelot, Alexandra,Piguel, Sandrine,Le Dour, Gwennael,Vidal, Joelle
, p. 9835 - 9838 (2003)
The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(O)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.