ArticleThe Journal of organic chemistry2023
Synergistic Li/Li Bimetallic System for the Asymmetric Synthesis of Antituberculosis Drug TBAJ-587.
Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Targeting Latent Tuberculosis Using Hypoxia-Activated Prodrugs of Bedaquiline Analogues.ACS medicinal chemistry letters · 2026Article
- Cu-Catalyzed dynamic kinetic asymmetric allylation enabled enantioselective assembly of sterically congested triaryl tertiary alcohols.Nature communications · 2026Article
- Article
- Catalytic enantioselective total synthesis of antitubercular agents (-)-bedaquiline and (-)-sudapyridine enabled by dynamic kinetic resolution-asymmetric transfer hydrogenation.Chemical science · 2025Article
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Authors and funding
7 authors.
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Abstract
TBAJ-587, an analogue of the antituberculosis drug bedaquiline (BDQ), bearing a diarylquinoline skeleton retains the high bacterial potency, is less toxic, and has a better pharmacokinetic profile than the parent molecule, which has entered phase I clinical trials. In contrast to its fascinating bioactivity, however, the highly efficient synthesis of this molecule is still an unsolved challenge. Herein, the first asymmetric synthesis of TBAJ-587 based on a synergistic Li/Li bimetallic system is reported. The product could be obtained in an excellent yield of 90% and an enantiomeric ratio (er) of 80:20. Furthermore, the reaction could be conducted on a 5 g scale, and the product was obtained with 99.9:0.1 er after a simple recrystallization. The realization of this protocol will greatly aid the demand for clinical drug production.
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