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Published on: October 2, 2018
Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant
Martin Riemer1, Veselina V Uzunova, Nastja Riemer
1Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK. m.shipman@warwick.ac.uk.
Abstract:
The first total synthesis of phyllostictine A (PA) is reported, which confirms the structure of this fungal metabolite and its (6S,7R,8S)-stereochemistry. Both synthetic PA and an analogue containing the 5-methylene-1,5-dihydro-2H-pyrrol-2-one nucleus exhibit μM inhibitory activity in root growth assays against Arabidopsis thaliana, indicating that this heterocyclic subunit is key to the herbicidal activity of the natural product.
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