Open AccessSynthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction
Author(s) -
Storm Hassell-Hart,
Elisa Speranzini,
Sirihathai Srikwanjai,
Euan J. Hossack,
S. Mark Roe,
D. Fearon,
Daniel Akinbosede,
S. Hare,
John Spencer
Publication year - 2022
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.2c02996
Subject(s) - chemistry , thiazole , ylide , substituent , catalysis , combinatorial chemistry , iridium , insertion reaction , stereochemistry , organic chemistry
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.