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Total synthesis of anithiactins A-C and thiasporine A
- Vaaland, I. Caroline, Lindbäck, Emil, Sydnes, Magne O.
- Tetrahedron letters 2019 v.60 no.8 pp. 610-612
- Suzuki reaction, alkylation, aminolysis, chemical structure, hydrolysis, organic compounds
- The total syntheses of anithiactins A-C (1–3) and thiasporine A (4) have been achieved in good overall yields. The key reaction in the synthetic sequence was the Suzuki-Miyaura cross-coupling between 2-aminophenylboronic acid hydrochloride and methyl 2-bromothiazole-4-carboxylate forming the common intermediate methyl 2-(2-aminophenyl)thiazole-4-carboxylate (8), which could be further transformed by hydrolysis, alkylation, and aminolysis to give the four title natural products. This work represents the first total synthesis of anithiactin B (2) and C (3).