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One features a stereoselective reduction followed by an asymmetric epoxidation sequence to set the vicinal diol stereocentres. The dienyne was installed via a one\u2010pot Wittig olefination and base\u2010mediated epoxide ring opening cascade. The other approach installed the diol through an asymmetric dihydroxylation reaction followed by a Horner\u2010Wadsworth\u2010Emmons olefination to afford the common dienyne intermediate. Finally, a Sonogashira coupling and an alkyne hydrosilylation\/proto\u2010desilylation protocol furnished LXB<jats:sub>4<\/jats:sub> in 25\u2009% overall yield in just 10\u2005steps. For the first time, LXB<jats:sub>4<\/jats:sub> has been fully characterized spectroscopically with its structure confirmed as previously reported. We have demonstrated that the synthesized LXB<jats:sub>4<\/jats:sub> showed similar biological activity to commercial sources in a cellular neuroprotection model. This synthetic route can be employed to synthesize large quantities of LXB<jats:sub>4<\/jats:sub>, enable synthesis of new analogs, and chemical probes for receptor and pathway characterization.<\/jats:p>","DOI":"10.1002\/chem.202200360","type":"journal-article","created":{"date-parts":[[2022,5,2]],"date-time":"2022-05-02T02:09:26Z","timestamp":1651457366000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["A Stereocontrolled Total Synthesis of Lipoxin B4 and its Biological Activity as a Pro\u2010Resolving Lipid Mediator of Neuroinflammation"],"prefix":"10.1002","volume":"28","author":[{"given":"C.","family":"Frank Lee","sequence":"first","affiliation":[{"name":"Centre for Medicinal Chemistry and Drug Discovery Krembil Research Institute University Health Network  Toronto Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carla E.","family":"Brown","sequence":"additional","affiliation":[{"name":"Centre for Medicinal Chemistry and Drug Discovery Krembil Research Institute University Health Network  Toronto Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander J.","family":"Nielsen","sequence":"additional","affiliation":[{"name":"Centre for Medicinal Chemistry and Drug Discovery Krembil Research Institute University Health Network  Toronto Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Changmo","family":"Kim","sequence":"additional","affiliation":[{"name":"Donald K. 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