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

Amand, Séverine; Vallet, Marine; Guedon, Laura; Genta-Jouve, Grégory; Wien, Frank; Mann, Stéphane; Dupont, Joëlle; Prado, Soizic; Nay, Bastien

doi:10.1021/acs.orglett.7b01788

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

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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.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002D-BD5D-5

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.