Synthesis of isoxazoline-substituted symmetrical diketopiperazines

Kyung Ho Park, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


A synthesis of racemic isoxazoline substituted symmetrical diketopiperazines has been achieved by twice utilizing a diastereoselective 1,3-dipolar cycloaddition step - mediated by intermolecular hydrogen-bonds between the Boc-NH of 2 and the requisite nitrile oxide (RCN+-O-) - to control alkene face selectivity. Dehydrative cyclization of the amide-linked amino acid 6 delivered diketopiperazine 8.

Original languageEnglish (US)
Pages (from-to)1267-1270
Number of pages4
Issue number9 SPEC. ISS.
StatePublished - 2003


  • 1,3-dipolar cycloaddition
  • Diketopiperazine (DKP)
  • Isoxazoline
  • Isoxazoline-substituted symmetrical DKPs

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'Synthesis of isoxazoline-substituted symmetrical diketopiperazines'. Together they form a unique fingerprint.

Cite this