A new and efficient method for the synthesis of various aza‐fused poly‐hetero aromatics has been described. This protocol includes an intermolecular condensation followed by metal‐free base‐promoted intramolecular C―N coupling reaction. The advantage of this one‐pot transformation lies in the use of simple cyclic amidines‐like compounds without prefunctionalization of the starting heterocycles.
An efficient and improved synthesis of a novel anti‐inflammatory drug, Lifitegrast 1 is described from Benzofuran‐6‐carboxylicacid. This synthetic approach avoided the racemization, formation of dimer impurities and furnished higher overall yield (79 %) with high purity. The key step of the synthesis involves tertiary butylester protection of the aminoacid fragment, which was hydrolyzed in further stages under mild acidic conditions. The critical process parameters were thoroughly studied for protection and deprotection of the tertiary butyl functional group. The attractive features of synthesis are the usage of commercially cheaper and eco‐friendly reagents suitable for multi kilo scale synthesis of Lifitegrast 1.
A new scalable synthesis of the common thiazole fragment (C12–C21 unit) of epothilone family of molecules (epothilone A–D) has been developed via palladium-catalyzed Wacker oxidation as a key step using (S)-2,2,3,3,9,9,10,10-octamethyl-5-vinyl-4,8-dioxa-3,9-disilaundecane, which has been prepared from commercially available chiral synthon (R)-ethyl-4-cyano-3-hydroxybutanoate. Then further chemical modifications using Horner–Wadsworth–Emmons reaction and Wittig reaction result in the common thiazole fragment (C12–C21 unit) in good yields.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.