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

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 as...

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Autores principales: Riemer, Martin, Uzunova, Veselina V., Riemer, Nastja, Clarkson, Guy J., Pereira, Nicole, Napier, Richard, Shipman, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6018569/
https://www.ncbi.nlm.nih.gov/pubmed/29897060
http://dx.doi.org/10.1039/c8cc03349h
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author Riemer, Martin
Uzunova, Veselina V.
Riemer, Nastja
Clarkson, Guy J.
Pereira, Nicole
Napier, Richard
Shipman, Michael
author_facet Riemer, Martin
Uzunova, Veselina V.
Riemer, Nastja
Clarkson, Guy J.
Pereira, Nicole
Napier, Richard
Shipman, Michael
author_sort Riemer, Martin
collection PubMed
description 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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spelling pubmed-60185692018-10-11 Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition Riemer, Martin Uzunova, Veselina V. Riemer, Nastja Clarkson, Guy J. Pereira, Nicole Napier, Richard Shipman, Michael Chem Commun (Camb) Chemistry 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. Royal Society of Chemistry 2018-07-04 2018-06-13 /pmc/articles/PMC6018569/ /pubmed/29897060 http://dx.doi.org/10.1039/c8cc03349h Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Riemer, Martin
Uzunova, Veselina V.
Riemer, Nastja
Clarkson, Guy J.
Pereira, Nicole
Napier, Richard
Shipman, Michael
Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
title Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
title_full Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
title_fullStr Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
title_full_unstemmed Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
title_short Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
title_sort phyllostictine a: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6018569/
https://www.ncbi.nlm.nih.gov/pubmed/29897060
http://dx.doi.org/10.1039/c8cc03349h
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