Practical enantioselective synthesis of a COX-2 specific inhibitor

Lushi Tan, Cheng Yi Chen, Weirong Chen, Lisa Frey, Anthony O. King, Richard D. Tillyer, Feng Xu, Dalian Zhao, Edward J.J. Grabowski, Paul J. Reider, Paul O'Shea, Philippe Dagneau, Xin Wang

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from (S)-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric acid and a novel thionyl chloride aided formation of amide 11 from acid 6.

Original languageEnglish (US)
Pages (from-to)7403-7410
Number of pages8
JournalTetrahedron
Volume58
Issue number37
DOIs
StatePublished - Sep 9 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • COX-2 inhibitor
  • Hydroxy ketone
  • Resolution
  • Suzuki coupling

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    Tan, L., Chen, C. Y., Chen, W., Frey, L., King, A. O., Tillyer, R. D., Xu, F., Zhao, D., Grabowski, E. J. J., Reider, P. J., O'Shea, P., Dagneau, P., & Wang, X. (2002). Practical enantioselective synthesis of a COX-2 specific inhibitor. Tetrahedron, 58(37), 7403-7410. https://doi.org/10.1016/S0040-4020(02)00826-8