Synthesis of 5-(S)-HETE, 5-(S)-HEPE and (+)-zooxanthellactone: Three hydroxylated polyunsaturated fatty acid metabolites

Abstract

Short and stereoselective syntheses of the two hydroxylated polyunsaturated fatty acid metabolites, namely 5-(S)-HETE and 5-(S)-HEPE, are reported in 23% and 30% overall yields, respectively. In addition, synthesis of the polyunsaturated fatty acid natural product (+)-zooxanthellactone has been achieved in 19% overall yield. The three aforementioned compounds have been conveniently prepared in six steps, starting from the corresponding commercially available polyunsaturated fatty acids arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid, respectively. All three hydroxylated polyunsaturated natural products were prepared using a biomimetic synthesis.

Keywords: 5-(S)-HDHA; 5-(S)-HEPE; 5-(S)-HETE; Polyunsaturated fatty acids; Stereoselective reduction of enone.