First Total Synthesis Of 4(r),17(r)-resolvin D6 Stereoisomer, A Potent Neuroprotective Docosanoid
The first total synthesis of a novel neuroprotective Resolvin D6 enantiomer, 4(R),17(R)-Resolvin D6, is described. Resolvin D6 is a lipid mediator derived from docosahexaenoic acid (DHA, C22:6, ω-3) with anti-inflammatory properties. Key synthetic features include the use of a MacMillan enantioselective organocatalytic α-oxidation of aldehydes in conjunction with a chiral pool-based approach to generate chiral synthons, a 1,4‑enyne unit as a linchpin, as well as a (Z)-selective Wittig coupling to assemble the Resolvin D6 core carbon skeleton.
Nshimiyimana, Robert; Fung Lam, Ting; Aggarwal, Shubhangi; Bazan, Nicolas; Bazan, Haydee E.P.; and Petasis, Nicos A., "First Total Synthesis Of 4(r),17(r)-resolvin D6 Stereoisomer, A Potent Neuroprotective Docosanoid" (2022). School of Medicine Faculty Publications. 572.