A straightforward synthesis of (E)-δ-alkenyl-β,γ-unsaturated δ-lactones by a tandem ring-closing/cross-coupling metathesis process

Marie-Alice Virolleaud (1) , Cyril Bressy (1) , Piva Olivier (1)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires

The access to (E)-δ-alkenyl-β,γ-unsaturated δ-lactones starting from 3-O-(1,4-pentadienyl) 3-butenoate has been investigated by using a tandem process including two different metathesis reactions. By this way, new structures, isomers of natural compounds like argentilactone, were isolated in good yields. Reconjugation of the internal CC bond can be achieved under basic conditions to give α-pyrones.

Domaines: Chimie organique

Marie-Alice Virolleaud, Cyril Bressy, Piva Olivier. A straightforward synthesis of (E)-δ-alkenyl-β,γ-unsaturated δ-lactones by a tandem ring-closing/cross-coupling metathesis process. Tetrahedron Letters, 2003, 44 (44), pp.8081-8084. ⟨10.1016/j.tetlet.2003.09.056⟩. ⟨hal-03232802⟩