American Chemical Society
jo2c00886_si_001.pdf (20.19 MB)

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

Download (20.19 MB)
journal contribution
posted on 2022-07-22, 13:41 authored by Ajay Sharma, Satyendra Kumar Pandey
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 Jørgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.