Synthesis of (+)-coniceine via reductive photocyclization of dienamides : an entry to indolizidines

Thomas Hjelmgaard (1, 2) , Daniel Gardette (1) , David Tanner (2) , David J Aitken (1, 3)

1 SEESIB - Synthèse et étude de systèmes à intêret biologique
2 Department of Chemistry
3 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

This paper describes the establishment of a new synthetic route to the hydrobromide salt of (+)-coniceine 1 with high enantiopurity in five steps and 8% overall yield. The key step is the reductive photocyclization of an acyclic chiral dienamide, for which a convenient one-pot synthesis is described.

Domaines: Chimie organique

Thomas Hjelmgaard, Daniel Gardette, David Tanner, David J Aitken. Synthesis of (+)-coniceine via reductive photocyclization of dienamides : an entry to indolizidines. Tetrahedron: Asymmetry, 2007, 18, pp.671-678. ⟨10.1016/j.tetasy.2007.03.004⟩. ⟨hal-00141843⟩