Synthesis of isoxazoline-substituted symmetrical diketopiperazines

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

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

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
JournalSynlett
Issue number9 SPEC. ISS.
StatePublished - 2003

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Park, K. H., Olmstead, M. M., & Kurth, M. J. (2003). Synthesis of isoxazoline-substituted symmetrical diketopiperazines. Synlett, (9 SPEC. ISS.), 1267-1270.