A Concise Total Synthesis of the Fungal Isoquinoline Alkaloid TMC-120B
2022
Ahmad K. Haidar | Niels D. Kjeldsen | Nikolaj S. Troelsen | Viola Previtali | Kasper P. Lundquist | Thomas O. Larsen | Mads H. Clausen
Recent reports of antiepileptic activity of the fungal alkaloid TMC-120B have renewed the interest in this natural product. Previous total syntheses of TMC-120B comprise many steps and have low overall yields (11&ndash:17 steps, 1.5&ndash:2.9% yield). Thus, to access this compound more efficiently, we herein present a concise and significantly improved total synthesis of the natural product. Our short synthesis relies on two key cyclization steps to assemble the central scaffold: isoquinoline formation via an ethynyl-imino cyclization and an intramolecular Friedel-Crafts reaction to form the furanone.
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