9(S)-hydroxyoctadecadienoic acid (9(S)-HODE) and 9,10,13-trihydroxyoctadecenoic acid (9(S),10(S),13(S)-TriHOME), endogenous metabolites biosynthesized from linoleic acid by 15-lipoxygenase (15-LOX), are gaining increasing importance due to their involvement in human diseases. However, the structural modification of 9(S)-HODE and 9(S),10(S),13(S)-TriHOME in biological and pharmaceutical applications remains largely unexplored. Herein we report the stereoselective synthesis of 9(S)-HODE and the first total synthesis of 9(S),10(S),13(S)-TriHOME. The synthesis of 9(S)-HODE began with the preparation of hept-1-yne and an enantiomerically enriched vinyl iodide. Sonogashira coupling, followed by semi-hydrogenation and hydrolysis, afforded 9(S)-HODE in 4 steps (44% overall yield, 99% ee). A chiral vinyl iodide was synthesized from azelaic anhydride in 8 steps with a 13% overall yield. The synthesis of 9(S),10(S),13(S)-TriHOME began with Sonogashira coupling of (S)-oct-1-yn-3-ol and (E)-vinyl iodide to the corresponding enyne. Sharpless asymmetric dihydroxylation provided the vicinal diol. Subsequent reactions, such as (E)-selective alkyne reduction and final deprotection followed by oxidation, afforded 9(S),10(S),13(S)-TriHOME in 9 steps (8% overall yield, ee ≥ 99.5%). In conclusion, the stereoselective synthesis of 9(S)-HODE was achieved in 12 steps (5.5% overall yield, 99% ee) and 9(S),10(S),13(S)-TriHOME was prepared in 15 steps (2.6% overall yield, ee ≥ 99.5%).