Synthesis of peptidomimetics, δ- and ε-lactam tetrazoles

Mol Divers. 2012 Aug;16(3):601-6. doi: 10.1007/s11030-012-9373-2. Epub 2012 May 24.

Abstract

A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1'-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl(2) activation to enable lactam formation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Chemistry Techniques, Synthetic
  • Diterpenes, Kaurane / chemistry
  • Lactams / chemistry*
  • Peptidomimetics / chemical synthesis*
  • Peptidomimetics / chemistry*
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / chemistry*

Substances

  • 5-oxokaurenoic acid
  • Diterpenes, Kaurane
  • Lactams
  • Peptidomimetics
  • Tetrazoles