Toxoplasma gondii: inhibitory activity and encystation effect of securinine and pyrrolidine derivatives on Toxoplasma growth.

Securinine, an alkaloid originally isolated from Securinega suffruticosa, exhibits a wide range of biological activities, including anti-malarial activity. Along with securinine, 10 pyrrolidine derivatives, generated via the retrosynthesis of (-)-securinine, were selected and tested for their inhibitory activity against Toxoplasma gondii growth in vitro. Anti-Toxoplasma activity correlated to hydrophobicity of the tested compounds.

The asymmetric total synthesis of (-)-securinine.

The alkaloid (-)-securinine was synthesized in 18 steps and 16% overall yield from trans-4-hydroxy-l-proline.

Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst.

A variety of aryl and heteroaryl bromides were cross-coupled with ammonia in good to high yields in the presence of a copper-NHC catalyst.

Acyclic diaminocarbenes: simple, versatile ligands for cross-coupling reactions.

Acyclic diaminocarbenes are found to be useful ligands for palladium catalyzed Suzuki-Miyaura, Sonogashira and Heck cross-coupling reactions of aryl/alkenyl bromides and chlorides.

Diastereoselective allylation and crotylation of N-unsubstituted imines derived from ketones.

A wide variety of tertiary carbinamines are synthesized in high yields via diastereoselective allylation and crotylation of in situ generated N-unsubstituted ketimines.