The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172)

Olefin metathesis
(OM) is a reliable and practical synthetic methodology
for challenging carbon–carbon bond formations. While existing
catalysts can effect many of these transformations, the synthesis
and development of new catalysts is essential to increase the application
breadth of OM and to achieve improved catalyst activity. The unexpected
initial discovery of a novel olefin metathesis catalyst derived from
synthetic efforts toward the HCV therapeutic agent grazoprevir (MK-5172)
is described. This initial finding has evolved into a class of tunable,
shelf-stable ruthenium OM catalysts that are easily prepared and exhibit
unique catalytic activity.