Synthesis of Fatty Acid Intermediates via Hudrlik–Peterson Reaction

The Hudrlik–Peterson Reaction of Secondary cis-TMS-Epoxy Alcohols and its Application to the Synthesis of the Fatty Acid Intermediates: S. Saito, Y. Nanba, M. Morita, Y. Kobayashi
Synlett 2019, DOI: 10.1055/s-0037-1611809

Polyunsaturated fatty acids are very important bioactive molecules, involved in a number of biochemical and physiological processes relevant to unmet medical needs, such as cardiovascular pathologies, cancer and neurodegenerative disorders. Despite their apparent structural simplicity – especially compared to other classes of extensively functionalized biologically relevant compounds – their synthesis is often challenging and requires complex and lengthy multi-step approaches, almost invariably plagued by low overall yields. Recently, the group of Professor Yuichi Kobayashi from the Tokyo Institute of Technology (Japan) came up with a novel strategy for the preparation of fatty acid intermediates, relying on the stereocontrolled Hudrlik–Peterson olefination reaction.  

Professor Kobayashi said: “This transformation is a new and practical method to give cis-enynyl alcohols based on the reaction that is specific to TMS-bearing epoxides. The products would be useful for the synthesis of biologically active compounds, especially metabolites derived from polyunsaturated fatty acids such as EPA and DHA.”