Synthesis of 13,19,20-Trihydroxy Docosahexaenoic Acid Stereoisomers

Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid: N. Ogawa, S. Sone, S. Hong, Y. Lu, Y. Kobayashi

Synlett 2020, 31, DOI: 10.1055/s-0040-1706415


The ω-3 fatty acid docosahexaenoic acid (DHA) is a key component of the central nervous system, as well as of skin and retina. Different DHA metabolites have shown therapeutic and preventive properties towards inflammation, as well as wound-healing activity. There is increasing interest towards stereopure DHA derivatives; however, there are significant challenges connected with their synthesis. Recently, the group of Professor Narihito Ogawa from Meiji University (Kanagawa, Japan), in collaboration with colleagues from Louisiana State University (New Orleans, USA), reported a multi-step stereoselective approach to trihydroxylated DHA analogues.

Professor Ogawa said: “We achieved the stereoselective synthesis of two stereoisomers of the 13,19,20-trihydroxy derivative of docosahexaenoic acid. In the future, the synthetic compounds will be used for drug discovery research.”

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