Late‐stage Rh(II)‐catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogs with Enhanced Antiproliferative Activity
Résumé
A set of new guaianolide derivatives (1-9) was obtained from Ludartin, Achalensolide and 11,13-Dihydroachalensolide by application of catalytic nitrene transfer reactions. Intermolecular nitrene C(sp 3)-H insertions led to the amination of C-1, C-2 and C-10 positions, while alkene aziridination was also observed under these reaction conditions. The antiproliferative activity of natural compounds and their derivatives was evaluated against a panel of human solid tumour cell lines. The results show that an increase in the biological activity was observed following amination at the C-2 position of Ludartin, thereby demonstrating the interest of late-stage C-H amination to improve the bioactivity of natural products.
Domaines
Chimie organiqueOrigine | Fichiers produits par l'(les) auteur(s) |
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