4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 54, Issue 52, Pages 7211-7214

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc03349h

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Funding

  1. EPSRC [EP/K031783/1]
  2. BBSRC
  3. EU
  4. Marie-Sklodowska-Curie Individual Fellowship [MSCA-IF-EF-4887, 705079]
  5. Research Councils UK
  6. EPSRC [EP/L027100/1, EP/K031783/1] Funding Source: UKRI
  7. Marie Curie Actions (MSCA) [705079] Funding Source: Marie Curie Actions (MSCA)

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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 lM 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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