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Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition

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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.

Graphical abstract: Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition

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Publication details

The article was received on 25 Apr 2018, accepted on 14 May 2018 and first published on 13 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC03349H
Citation: Chem. Commun., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition

    M. Riemer, V. V. Uzunova, N. Riemer, G. J. Clarkson, N. Pereira, R. Napier and M. Shipman, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC03349H

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