Stereoselective synthesis of functionalized pyroglutamates

Matthew J. Just, Srinivas Tekkam, Mohammad A. Alam, Subash C. Jonnalagadda, Joseph L Johnson, Venkatram R Mereddy

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Novel stereoselective synthesis of α-methylene-β-substituted pyroglutamates, and α-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of l-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells.

Original languageEnglish (US)
Pages (from-to)5349-5351
Number of pages3
JournalTetrahedron Letters
Volume52
Issue number41
DOIs
StatePublished - Oct 12 2011

Bibliographical note

Funding Information:
We thank the Departments of Chemistry and Biochemistry, University of Minnesota Duluth and Rowan University for the funding. Partial support for this work was also provided by research grants from the University of Minnesota Academic Health Center Faculty Development Grant (V.R.M.), Whiteside Institute for Clinical Research (V.R.M.), and Rowan University Non-Salary Financial Support Grants (NSFSG) (S.C.J.). We thank Dr. Victor G. Young, Jr. (University of Minnesota X-ray Crystallographic Laboratory) for providing the crystal structure.

Keywords

  • Baylis-Hillman bromides/acetates
  • Oxazoles
  • Pyroglutamates (γ-carboxy-γ-lactams)
  • Substrate controlled alkylation
  • Threonine

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