Organocatalyzed Protecting-Group-Free Total Synthesis of (S,S)- and (S,R)-Reboxetine, an Antidepressant Drug

An efficient, simple, and concise organocatalyzed protecting-group free synthetic approach to the stereoisomers of the antidepressant drug reboxetine and its implementation toward the asymmetric synthesis of (S,S)-reboxetine and (S,R)-reboxetine from commercially available trans-cinnamaldehyde are described. The synthesis features organocatalytic Jorgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.

Automated summary

An efficient and concise organocatalyzed protecting-group free synthetic approach is described for synthesizing the stereoisomers of the antidepressant drug reboxetine. The synthesis involves organocatalytic Jorgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.