Late-stage Rh(II)-catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogues with Enhanced Antiproliferative Activity.

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(sp3)—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.

Références

Titre
Late-stage Rh(II)-catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogues with Enhanced Antiproliferative Activity.
Type de publication
Article de revue
Année de publication
2021
Revue
European Journal of Organic Chemistry
Ticket
12
Pagination
1859-1863
Soumis le 15 février 2021