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

Oleg A Lozinski; J Bistodeau; C Bennetau-Pelissero; Vladimir P Khilya; S Shinkaruk

doi:10.1007/s00706-020-02584-8

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

Monatsh Chem. 2020;151(4):605-610. doi: 10.1007/s00706-020-02584-8. Epub 2020 Apr 28.

Authors

Oleg A Lozinski^{1

2

3}, J Bistodeau², C Bennetau-Pelissero⁴, Vladimir P Khilya¹, S Shinkaruk²

Affiliations

¹ Taras Shevchenko National University of Kyiv, Kyiv, Ukraine.
² University of Bordeaux, ISM, UMR 5255, CNRS, Bordeaux, France.
³ University of Bordeaux, Neurocentre Magendie, UMR 1215, INSERM, Bordeaux, France.
⁴ University of Bordeaux, ARNA, UMR 1212, INSERM/CNRS, Bordeaux, France.

Abstract

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.

Keywords: Alkenes; Flavonoids; Heterocycles; Metathesis; Prenyl.