J. Org. Chem. [SOPHY]

Abstract:

A synthesis of new-to-nature aza-iridoids via ynamides is presented. ZrCl₄ proved to be the best acid to perform this transformation. Various ynamides were accommodated, and seco-iridoids could be obtained as well. Aza-iridoids were infiltrated into leaves of Scrophularia Nodosa, an iridoid-producing plant species. High-resolution mass spectrometry coupled to computational metabolomic approaches was employed for the detection of aza-iridoid bioconversion products.

Reference :

Baptiste Moegle, Maxime Hourtoule, Clément Gommenginger, Asmaa Belabbes, Claire Villette, David Elser, Emmanuel Gaquerel, Nicolas Navrot, and Laurence Miesch

Synthesis of Non-natural Aza-Iridoids via Ynamides and Molecular Networking-Based Tracing of Their In Planta Bioconversion

J. Org. Chem. First published: 12 May 2022, DOI: https://doi.org/10.1021/acs.joc.2c00445

 

Contact:

Laurence Miesch, équipe SOPhy, Institut de Chimie (UMR 7177).