Journal
TETRAHEDRON LETTERS
Volume 52, Issue 41, Pages 5349-5351Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.08.029
Keywords
Pyroglutamates (gamma-carboxy-gamma-lactams); Threonine; Oxazoles; Substrate controlled alkylation; Baylis-Hillman bromides/acetates
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Funding
- Departments of Chemistry and Biochemistry, University of Minnesota Duluth
- Rowan University
- University of Minnesota Academic Health Center
- Whiteside Institute for Clinical Research
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Novel stereoselective synthesis of alpha-methylene-beta-substituted pyroglutamates, and alpha-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. (C) 2011 Elsevier Ltd. All rights reserved.
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