Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides

Sébastien Prevost (1, 2, 3) , Ambre Dezaire (4) , Alexandre Escargueil (4)

1 DCSO - Laboratoire de synthèse organique
2 MCAM - Molécules de Communication et Adaptation des Micro-organismes
3 Laboratoire Charles Friedel
4 CRSA - Centre de Recherche Saint-Antoine

An intramolecular aryne Diels-Alder reaction with a furan moiety was applied to the synthesis of dihydrobenzo[ de]isochromenes as intermediates toward naphthalimides. After oxidation, this method offers an efficient approach for the synthesis of substituted naphthalimides, which showed potent cytotoxic activity against HT-29 human cancer cell line.

Keywords: Antineoplastic Agents/chemical synthesis; Antineoplastic Agents/chemistry; Benzene Derivatives/chemistry; Cycloaddition Reaction; Furans/chemistry; Naphthalimides/chemical synthesis; Naphthalimides/chemistry

Domains: Chemical Sciences; Organic chemistry

Sébastien Prevost, Ambre Dezaire, Alexandre Escargueil. Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides. Journal of Organic Chemistry, 2018, 83 (8), pp.4871-4881. ⟨10.1021/acs.joc.8b00531⟩. ⟨hal-02091716⟩