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

Ahmad K. Haidar, Niels D. Kjeldsen, Nikolaj S. Troelsen, Viola Previtali, Kasper P. Lundquist, Thomas O. Larsen, Mads H. Clausen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

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.
Original languageEnglish
Article number521
JournalMolecules
Volume27
Issue number2
Number of pages9
ISSN1420-3049
DOIs
Publication statusPublished - 2022

Keywords

  • Isoquinolines
  • Alkaloids
  • Epilepsy

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