A Concise Total Synthesis of the Fungal Isoquinoline Alkaloid TMC-120B |
| |
| Authors: | Ahmad K. Haidar Niels D. Kjeldsen Nikolaj S. Troelsen Viola Previtali Kasper P. Lundquist Thomas O. Larsen Mads H. Clausen |
| |
| Affiliation: | 1.Center for Nanomedicine and Theranostics, Department of Chemistry, Technical University of Denmark, Kemitorvet 207, 2800 Kongens Lyngby, Denmark; (A.K.H.); (N.S.T.); (V.P.); (K.P.L.);2.NCK A/S, Rugmarken 28, 3520 Farum, Denmark;3.Department of Biotechnology and Biomedicine, Technical University of Denmark, Søltofts Plads, Building 221, 2800 Kongens Lyngby, Denmark; |
| |
| 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. |
| |
| Keywords: | isoquinolines alkaloids epilepsy |
|
|
