On the Total Synthesis of 7,8(S,S)-Epoxy-17(S)-hydroxy-4(Z),9(E),11(E),13(Z),15(E),19(Z)-docosahexaenoic Acid Derivative
2025
The stereoselective total synthesis of an allylic epoxide-containing polyunsaturated fatty acid, in its triethylsilyl (TES) ether and methyl ester form, is described. Key features include a Sharpless enantioselective epoxidation to install the oxirane unit and Wittig coupling reactions to forge critical alkenyl configuration and secure the core carbon skeleton. The deprotected epoxy acid was recently demonstrated to play a central role as the precursor to biologically active resolvins D1, D2, and the cysteinyl con…