A Concise Total Synthesis of the Fungal Isoquinoline Alkaloid TMC-120B

Autor: Ahmad K. Haidar, Niels D. Kjeldsen, Nikolaj S. Troelsen, Viola Previtali, Kasper P. Lundquist, Thomas O. Larsen, Mads H. Clausen
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Molecules, Vol 27, Iss 2, p 521 (2022)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules27020521
Popis: 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 (11–17 steps, 1.5–2.9% 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.
Databáze: Directory of Open Access Journals
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