LOZINSKI, Oleg A.; BISTODEAU, J.; BENNETAU-PELISSERO, Catherine; KHILYA, Vladimir P.; SHINKARUK, Svitlana

doi:10.1007/s00706-020-02584-8

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LOZINSKI, Oleg A.
Neurocentre Magendie : Physiopathologie de la Plasticité Neuronale [U1215 Inserm - UB]

BISTODEAU, J.
Institut des Sciences Moléculaires (Bordeaux)

BENNETAU-PELISSERO, Catherine
Université de Bordeaux [UB]
Acides Nucléiques : Régulations Naturelle et Artificielle [ARNA]

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Monatshefte fur Chemie. 2020, vol. 151, n° 4, p. 605-610

Résumé en anglais

Abstract: The multistep synthesis of a prenylneoflavone through a sequence of the Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis reaction has been accomplished in 5% yield over six steps starting from commercially available 3-methoxyacetophenone. The sequence is shown to be compatible with a Pechmann condensation which proved to be a robust and cost-effective method for the assembling of the α-pyrone core. The results open doors to a general approach to the prenylneoflavone system starting from phenol and acetophenone derivatives. Graphic abstract: [Figure not available: see fulltext.] © 2020, Springer-Verlag GmbH Austria, part of Springer Nature.< Réduire

Mots clés en anglais

Alkenes

Flavonoids

Heterocycles

Metathesis

Prenyl