Abstract
γ‐Linolenic (GLA; C18 : 3 n‐6), dihomo‐γ‐linolenic (DGLA; C20 : 3 n‐6) and stearidonic (SDA; C18 : 4 n‐3) acids are found in several botanic and marine oils and are sustainable sources of omega‐6 and omega‐3 polyunsaturated fatty acids (PUFAs). During oxidative stress (pollution, UV, hydric or nutrient stress), lipid peroxidation occurred to produce non‐enzymatic oxylipins named phytoprostanes (PhytoPs). We report herein the first syntheses of six non‐enzymatic PUFA metabolites originated from GLA, DGLA and SDA peroxidation. Our syntheses follow a straightforward synthetic pathway from enantiopure common intermediates (lactol or monoacetates), further used Horner‐Wadsworth‐Emmons and Wittig reactions to set up the side chains, and Corey‐Bakshi‐Shibata enantioselective reduction. Our strategy once again proved to be highly efficient as the compounds were obtained after only 4 to 12 consecutive steps, starting from previously prepared intermediates, and in a range from 6.5 to 41.5 % yield.