Construction of spirolactones with concomitant formation of the fused quaternary centre - application to the synthesis of natural products

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

1 STeRéO

Polycyclic structures fused at a central carbon are of great interest due to their appealing conformational features and their structural implications in biological systems. Although progress in the development of synthetic methodologies towards such structures has been impressive, the stereoselective construction of such quaternary stereocentres remains a significant challenge in the total synthesis of natural products. This review highlights the progress in the formation of 1- oxaspiro[4.n]alkan-2-ones with concomitant formation of the quaternary spiro centre.

Mots clés: spirolactone; quaternary centre; natural product

Domaines: Chimie organique

Alexandra Bartoli, Fabien Rodier, Laurent Commeiras, Jean-Luc Parrain, Gaëlle Chouraqui. Construction of spirolactones with concomitant formation of the fused quaternary centre - application to the synthesis of natural products. Natural Product Reports, 2011, 28, pp.763-782. ⟨10.1039/C0NP00053A⟩. ⟨hal-00681321⟩