Synthesis of the Enantiomers of Thioridazine
Synthesis of the Enantiomers of Thioridazine: S. Antonsen, E. B. Monsen, K. Ovchinnikov, J. M. J. Nolsøe, D. Ekeberg, J. E. Kristiansen, D. B. Diep, Y. Stenstrøm
SynOpen 2020, 4, 12–16
Thioridazine is a phenothiazine antipsychotic drug – withdrawn from the market in 2005 because of its side effects – which has also been recently shown to have promising antibacterial activity, including against drug resistant ones causing tuberculosis. The two enantiomers have significantly different biological activities; however, only a couple of syntheses exist for preparing thioridazine enantiomers. Recently, Professor Yngve Stenstrøm, Dr. Simen Antonsen and co-workers from the Norwegian University of Life Sciences (Ås, Norway) reported an auxiliary-based total synthesis of both enantiomers in high stereo-purity.
Dr. Antonsen said: “It is a simple synthetic strategy to give thioridazine in high enantiopurity. It is easy to carry out, can be easily scaled up, and is very useful for making larger quantities needed for biological studies.”