Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin

Sébastien Dubois (1) , Fabien Rodier (1) , Romain Blanc (1) , Raphaël Rahmani (1) , Virginie Héran (1) , Jérôme Thibonnet (2) , Laurent Commeiras (1) , Jean-Luc Parrain (1)

1 STeRéO
2 PCM2E - Physico-chimie des Matériaux et des Electrolytes pour l'Energie

An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2- disilyloxybenzocyclobutene and the appropriate γ-alkylidenebutenolide. The feasibility and the total chemoselectivity of the [4 + 2] cycloaddition for the construction of a spirolactone moiety via an intramolecular approach (IMDA) using both partners is also described demonstrating the versatility of the γ-alkylidenebutenolide building block.

Mots clés: Lactonamycine; diels-alder; ortho-quinodimethane

Domaines: Chimie organique

Sébastien Dubois, Fabien Rodier, Romain Blanc, Raphaël Rahmani, Virginie Héran, et al.. Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin. Organic & Biomolecular Chemistry, 2012, 10, pp.4712-4719. ⟨10.1039/c2ob25299f⟩. ⟨hal-00736663⟩