Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction

  • Org Lett. 2022 Nov 4;24(43):7924-7927. doi: 10.1021/acs.orglett.2c02996.
Storm Hassell-Hart  1 ,  Elisa Speranzini  1 ,  Sirihathai Srikwanjai  1 ,  Euan Hossack  2 ,  S Mark Roe  2 ,  Daren Fearon  3 ,  Daniel Akinbosede  2 ,  Stephen Hare  2 ,  John Spencer  1
Affiliations
  • 1. Department of Chemistry, School of Life Sciences, University of Sussex, Brighton BN1 9QJ, U.K.
  • 2. Department of Biochemistry, School of Life Sciences, University of Sussex, Brighton BN1 9QG, U.K.
  • 3. Diamond LightSource (DLS), Harwell Science and Innovation Campus, Didcot OX11 0DE, U.K.
PMID: 36265082 DOI: 10.1021/acs.orglett.2c02996
Abstract

A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.

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