A new access to the 6,8-dioxabicyclo[3.2.1]octane ring system using a three-component reaction : enantioselective synthesis of (+)-iso-exo-brevicomin

Asmae Bouziane (1) , Thomas Régnier (1) , François Carreaux (1) , Bertrand Carboni (1) , Christian Bruneau (1) , Jean-Luc Renaud (2)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCMT - Laboratoire de chimie moléculaire et thioorganique

The combination of a catalytic hetero-Diels-Alder-­allylboration sequence and a ruthenium-catalyzed isomerization of an allylic alcohol moiety as key steps open a new route for the asymmetric synthesis of 6,8-dioxabicyclo[3.2.1]octane subunits. The application of this strategy to the synthesis of (+)-iso-exo-brevi­comin is also reported.

Mots clés: natural product; asymmetric catalysis; cycloaddition; boron; redox isomerization

Domaines: Catalyse

Asmae Bouziane, Thomas Régnier, François Carreaux, Bertrand Carboni, Christian Bruneau, et al.. A new access to the 6,8-dioxabicyclo[3.2.1]octane ring system using a three-component reaction : enantioselective synthesis of (+)-iso-exo-brevicomin. SYNLETT, 2010, 2010 (2), pp.207-210. ⟨10.1055/s-0029-1218561⟩. ⟨hal-00492573⟩