Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence

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 compati...

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Detalles Bibliográficos
Autores principales: Lozinski, Oleg A., Bistodeau, J., Bennetau-Pelissero, C., Khilya, Vladimir P., Shinkaruk, S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2020
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7186117/
https://www.ncbi.nlm.nih.gov/pubmed/32346184
http://dx.doi.org/10.1007/s00706-020-02584-8
Descripción
Sumario: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: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-020-02584-8) contains supplementary material, which is available to authorized users.

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