| Autor: |
Das, Swagata, Paul, Sayan, Mandal, Kishor Kumar, Anoop, Anakuthil, Nanda, Samik |
| Zdroj: |
The Journal of Organic Chemistry; November 2024, Vol. 89 Issue: 21 p15764-15776, 13p |
| Abstrakt: |
Asymmetric total synthesis of naturally occurring 3-substituted isocoumarins, 2′-methoxydihydroartemidin, (E)-3′-hydroxyartemidin, and two structural congeners is reported in this article. Enantiopure 3-alkylisocoumarin core present in those target molecules was accessed through an atom-economical and regiodefined 6-endo-digcyclization from properly substituted 2-halobenzoic acids and chiral terminal alkynes through ligand-free Cu(I) catalysis. A detailed mechanistic investigation was carried out through control experiments, and density functional theory (DFT) analysis reveals that solvent directed a non-Sonogashira pathway through direct insertion of alkyne through a regiodefined way is operating. The synthesized 3-alkylisocoumarins are synthetically manipulated into various small molecular entities. |
| Databáze: |
Supplemental Index |
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