Synthesis of a thiazole library via an iridium-catalyzed sulfur ylide insertion reaction

DOI: 10.1021/acs.orglett.2c02996

Authors: Storm Hassell-Hart (University of Sussex) , Elisa Speranzini (University of Sussex) , Sirihathai Srikwanjai (University of Sussex) , Euan Hossack (University of Sussex) , S. Mark Roe (University of Sussex) , Daren Fearon (Diamond Light Source) , Daniel Akinbosede (University of Sussex) , Stephen Hare (University of Sussex) , John Spencer (University of Sussex)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Organic Letters , VOL 24 , PAGES 7924 - 7927

State: Published (Approved)
Published: November 2022

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.

Journal Keywords: Alkyls; Amines; Catalysts; Heterocyclic compounds; Substituents

Diamond Keywords: Bacteria

Subject Areas: Biology and Bio-materials, Chemistry, Medicine


Instruments: I04-1-Macromolecular Crystallography (fixed wavelength)

Added On: 09/11/2022 11:54

Documents:
acs.orglett.2c02996.pdf

Discipline Tags:

Pathogens Infectious Diseases Health & Wellbeing Biochemistry Chemistry Structural biology Organic Chemistry Drug Discovery Life Sciences & Biotech

Technical Tags:

Diffraction Macromolecular Crystallography (MX)