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  A reactive eremophilane and its antibacterial 2(1H)‑naphthalenone rearrangement product, witnesses of a microbial chemical warfare

Amand, S., Vallet, M., Guedon, L., Genta-Jouve, G., Wien, F., Mann, S., et al. (2017). A reactive eremophilane and its antibacterial 2(1H)‑naphthalenone rearrangement product, witnesses of a microbial chemical warfare. Organic Letters, 19(15), 4038-4041. doi:10.1021/acs.orglett.7b01788.

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 Creators:
Amand, Séverine, Author
Vallet, Marine1, Author              
Guedon, Laura, Author
Genta-Jouve, Grégory, Author
Wien, Frank, Author
Mann, Stéphane, Author
Dupont, Joëlle, Author
Prado, Soizic, Author
Nay, Bastien, Author
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1External Organizations, ou_persistent22              

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 Abstract: Two sesquiterpenes, 4-epimicrosphaeropsisin (1) and a dihydrofurano- 2(1H)-naphthalenone (variabilone, 2) which represents a new skeleton, were isolated from endophytic fungus Paraconiothyrium variabile. Reactivity studies showed that eremophilane 1 is a precursor of 2 through acid-promoted methyl 1,2-migration and aromatization. An electrophilic intermediate of this transformation was intercepted by N-acetylcysteamine, a biomimetic nucleophile. Only compound 2 was antibacterial against endophytic bacterium Bacillus subtilis (coisolated with P. variabile), suggesting a role in the microbial competition in plants.

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 Dates: 2017-07-24
 Publication Status: Published in print
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 Identifiers: Other: EXT490
DOI: 10.1021/acs.orglett.7b01788
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 19 (15) Sequence Number: - Start / End Page: 4038 - 4041 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338