A convenient and versatile synthesis of 6, 5- and 7, 5-fused bicyclic lactams as peptidomimetics

  • Zhang X
  • Jiang W
  • Schmitt A
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Abstract

Chemo-selective reduction of the pyroglutamate ring carbonyl in a serine-pyroglutamate or homoserine to pyroglutamate dipeptide gave a hemiaminal. Treatment of the hemiaminal with a catalytic amount of TFA in CH2Cl2generated an N-acyliminium ion that was intramolecularly trapped by the side-chain hydroxyl to give a 6, 5 or 7, 5-bicyclic lactam. © 2001 DuPont Pharmaceuticals Company.

Author-supplied keywords

  • 6, 5- and 7, 5-fused bicyclic lactams
  • N-acyliminium ion
  • Peptidomimetics

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Authors

  • Xiaojun Zhang

  • Wen Jiang

  • Aaron C. Schmitt

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