Monohydroxylated polyunsaturated fatty acids belonging to the oxylipin class of natural products are present in marine and terrestrial sources as well as in the human body. Due to their biological activities and role in diverse biosynthetic pathways, oxylipins biosynthesized from eicosapentaenoic acid and arachidonic acid have attracted great interest from the scientific community. One example is 3-hydroxyeicosapentaenoic acid where the absolute configuration at C-3 has only been tentatively assigned. In this paper, studies on acetate type aldol reactions that enabled the preparation of 3-(R)-hydroxyeicosapentaenoic acid (3R-HETE, 2) and its enantiomer are presented.
Keywords: 19F NMR Mosher esters analysis; 3-hydroxy eicosapentaenoic acid; Braun acetate aldol reaction; Nagao–Fujita acetate aldol reaction; docosahexaenoic acid; eicosanoids; eicosapentaenoic acid; oxylipins; stereoselective synthesis.