An active-site model of prostaglandin H synthase: An iron "twin-coronet" porphyrin with an aryloxyl radical overhang and its catalytic oxygenation of 1,4-diene

Impressions of enzymes: A stable naphthoxyl radical was formed in the cavity of an iron porphyrin by peroxy acid oxidation. The intermediate was characterized by spectroscopic methods. This reaction was applied to the catalytic oxygenation of Z, Z-1,4-diene regio- and stereoselectively to give the corresponding alcohol under an O₂ atmosphere (see picture). This is the first example of a mimic of the active site of the prostaglandin H synthases.