Intramolecular Imino Diels−Alder Reaction: Progress toward the Synthesis of Uncialamycin

Sandy Desrat (1) , Pierre van de Weghe (2)

1 ICSN - Institut de Chimie des Substances Naturelles
2 ISCR - Institut des Sciences Chimiques de Rennes

We herein described an intramolecular imino Diels−Alder reaction promoted with BF3·OEt2/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.

Domaines: Chimie; Chimie organique

Sandy Desrat, Pierre van de Weghe. Intramolecular Imino Diels−Alder Reaction: Progress toward the Synthesis of Uncialamycin. Journal of Organic Chemistry, 2009, 74 (17), pp.6728-6734. ⟨10.1021/jo901291t⟩. ⟨hal-02355118⟩