Synthesis of 6,5-Fused Bicyclic Lactams as Potential Dipeptide β-Turn Mimetics

Article abstract of DOI:10.1016/S0040-4039(00)73120-0

The first short synthesis of the dipeptide mimetic (3S,6S,9S)-6-amino-5-oxoindolizidine-3-carboxylic acid 1 and its Z-protected derivative 9 is described, employing the Schoellkopf bislactim-ether methodology, followed by a highly specific intramolecular reductive amination and spontaneous lactamization.These 6,5-fused bicyclic lactams may be viewed as comformationally restricted alanyl-proline β-turn mimetics.