Abstract:

JP4-039 1 (scheme 1) is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS). Only one synthesis is described in the literature, which consists of six steps and involves a one-pot hydrozirconation-transmetalation-addition to a chiral sulfinimine as the key step. As our group has been recently exploiting the chemistry of α,β-unsaturated diazoketones, we were interested in investigating these platforms for the direct synthesis of β,γ- unsaturated amides and apply the methodology to prepare the bioprotective agent JP4-039 in just one step from them.