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

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 ?M inhibitory activity in root growth assays against Arabidopsis thaliana, indicating that this heterocyclic subunit is key to the herbicidal activity of the natural product.

SUBMITTER: Riemer M

PROVIDER: S-EPMC6018569 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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

Riemer Martin M Uzunova Veselina V VV Riemer Nastja N Clarkson Guy J GJ Pereira Nicole N Napier Richard R Shipman Michael M

Chemical communications (Cambridge, England) 20180601 52

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. ...[more]

PMID: 29897060

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