Late‐stage Rh(II)‐catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogs with Enhanced Antiproliferative Activity - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

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 organique
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Dates et versions

hal-03344899 , version 1 (15-09-2021)

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Citer

Sebastián J Castro, José M. Padrón, Benjamin Darses, Viviana E Nicotra, Philippe Dauban. Late‐stage Rh(II)‐catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogs with Enhanced Antiproliferative Activity. European Journal of Organic Chemistry, 2021, 2021 (12), pp.1859-1863. ⟨10.1002/ejoc.202100074⟩. ⟨hal-03344899⟩
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