Solid-phase synthesis of beta-lactams via the Miller hydroxamate approach

Org Lett. 2001 Feb 8;3(3):337-40. doi: 10.1021/ol006779z.

Abstract

[figure: see text] beta-Lactams were prepared on solid phase starting from serine, threonine, or other beta-hydroxyacids derived from naturally occurring amino acids and a resin bound hydroxylamine. The ring closure was carried out under Mitsunobu conditions. The amino group present on the beta-lactam was used to assemble a short peptide. After a reductive cleavage with Sml2, beta-lactam-containing peptides were obtained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Hydroxamic Acids / chemistry*
  • Hydroxylamines
  • Polystyrenes
  • Serine / chemistry
  • Threonine / chemistry
  • beta-Lactams / chemical synthesis*

Substances

  • Anti-Bacterial Agents
  • Hydroxamic Acids
  • Hydroxylamines
  • Polystyrenes
  • beta-Lactams
  • Threonine
  • Serine