N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A

Florence Souquet (1) , Wassila Drici , Sandra Abi Fayssal , Imane Lazouni , Sébastien Thueillon , Joelle Pérard-Viret (1)

1 CiTCoM - UMR 8038 - Cibles Thérapeutiques et conception de médicaments

We describe an improved synthesis of unsaturated γ-lactams by condensation of various primary amines with 2,5-dimethoxy-2,5dihydrofuran. A modified mechanism for this reaction is suggested. Synthesis of their N-α-methoxylated derivatives, as N-acyliminium ions precursors, is also reported. Finally, a short synthesis of ()-crispine A is presented as an illustrative application.

Mots clés: unsaturated γ-lactams; aza-heterocycles; N-acyliminium; 5methoxypyrrolidin-2-one; crispine A

Domaines: Chimie thérapeutique; Chimie organique

Florence Souquet, Wassila Drici, Sandra Abi Fayssal, Imane Lazouni, Sébastien Thueillon, et al.. N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A. Synthesis: Journal of Synthetic Organic Chemistry, 2020, synthesis, pp.2970-2978. ⟨10.1055/s-0040-1707886⟩. ⟨hal-02890991⟩