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Late‐stage Rh(II)‐catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogs with Enhanced Antiproliferative Activity
Author(s) -
Castro Sebastián J.,
Padrón José M.,
Darses Benjamin,
Nicotra Viviana E.,
Dauban Philippe
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100074
Subject(s) - nitrene , amination , chemistry , catalysis , stereochemistry , alkene , combinatorial chemistry , organic chemistry
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 tumor 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 in late‐stage C−H amination to improve the bioactivity of natural products.