Total Synthesis of Fijiolide A
| Autor: | Christoph Heinz, Nicolai Cramer |
|---|---|
| Jazyk: | German<br />English<br />French |
| Rok vydání: | 2016 |
| Předmět: | |
| Zdroj: | CHIMIA, Vol 70, Iss 4 (2016) |
| Druh dokumentu: | article |
| ISSN: | 0009-4293 2673-2424 |
| DOI: | 10.2533/chimia.2016.258 |
| Popis: | Fijiolide A is a secondary metabolite isolated from a marine-derived actinomycete of the genus Nocardiopsis. It was found to significantly reduce the TNF-? induced activity of the transcription factor NF?B, which is considered a promising target for the treatment of cancer and inflammation-related diseases. We disclose an enantioselective synthesis of fijiolide A enabled by a fully intermolecular, yet regioselective cyclotrimerization of three unsymmetrical alkynes to construct its tetra-substituted arene core. An atropselective macroetherification enables the assembly of the strained [2.6]paracyclophane motif. A late-stage glycosylation of the macrocyclic aglycone at its tertiary alcohol position allowed for the first total synthesis of fijiolide A. |
| Databáze: | Directory of Open Access Journals |
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