The first total synthesis of the 10,11-dihydro-12-ketoeicosatetraenoic
acid (10,11-dihydro-12-KETE) 5, a proinflammatory metabolite of 12-KE
TE is reported. In addition, the total synthesis of two other potentia
l metabolites of 12-KETE, namely 8,11-dihydro-12-KETE 6 and 8,9-dihydr
o-12-KETE 7, is also described. These three synthetic compounds are ai
med at investigating a new biosynthetic reductive pathway for 12-hydro
xyeicosatetraenoic acid (12-HETE) and 12-KETE.