First studies directed towards the diastereoselective synthesis of the BCD tricyclic core of brownin F

Fabien Rodier (1) , Jean-Luc Parrain (1) , Gaëlle Chouraqui (1) , Laurent Commeiras (1)

1 STeRéO

The BCD tricyclic core of brownin F was prepared in eight synthetic operations for the first time. Our synthesis features a diastereo-, chemo- and regioselective intramolecular [3 + 2] cycloaddition between a cyclic carbonyl ylide and a γ-alkylidenebutenolide.

Mots clés: natural product; cycloaddition; butenolide

Domaines: Chimie organique

Fabien Rodier, Jean-Luc Parrain, Gaëlle Chouraqui, Laurent Commeiras. First studies directed towards the diastereoselective synthesis of the BCD tricyclic core of brownin F. Organic & Biomolecular Chemistry, 2013, 11, pp.4178-4185. ⟨10.1039/c3ob40363g⟩. ⟨hal-00861693⟩