Abstract
Ecteinascidin-743 (Trabectidin, Trabectedin ®, Yondelis ®) is a synthetically obtained pharmaceutical drug originally isolated from a marine tunicate. Trabectedin is used for the chemotherapy of soft-tissue sarcoma and ovarian cancer. The isoquinolinium metabolite ETM-204 has been found in biotransformation and degradation studies of Trabectedin. We report the first total synthesis of ETM-204 and its full spectroscopic characterization confirming the postulated structure. Central elements of the 12-step synthesis starting from 2-methyl-6-nitrophenol are a Cu-mediated conversion of an iodoarene to a phenol, a Skattebøl-formylation, and a modified Pomeranz–Fritsch cyclization to assemble the isoquinoline ring. The pH-dependence of its visual absorbance could be clarified. Graphic abstract: [Figure not available: see fulltext.]
Originalsprache | englisch |
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Seiten (von - bis) | 1327-1337 |
Seitenumfang | 11 |
Fachzeitschrift | Monatshefte für Chemie - Chemical Monthly |
Jahrgang | 154 |
Ausgabenummer | 12 |
Frühes Online-Datum | 19 Okt. 2021 |
DOIs | |
Publikationsstatus | Veröffentlicht - Dez. 2023 |
ASJC Scopus subject areas
- Chemie (insg.)
Fields of Expertise
- Human- & Biotechnology