Journal article
A Concise Total Synthesis of the Fungal Isoquinoline Alkaloid TMC-120B
Analytics, Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark1
Yeast Natural Products, Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark2
Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark3
Department of Chemistry, Technical University of Denmark4
NCK A/S5
Center for Microbial Secondary Metabolites, Centers, Technical University of Denmark6
Natural Product Discovery, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark7
Department of Biotechnology and Biomedicine, Technical University of Denmark8
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.
| Language: | English |
|---|---|
| Publisher: | MDPI AG |
| Year: | 2022 |
| Pages: | 521 |
| ISSN: | 14203049 and 14315157 |
| Types: | Journal article |
| DOI: | 10.3390/molecules27020521 |
| ORCIDs: | Troelsen, Nikolaj S. , 0000-0001-5396-336X , Lundquist, Kasper P. , Clausen, Mads H. , Haidar, Ahmad K. and Larsen, Thomas O. |
