{"doi":"10.1002/chem.202200360","title":"A Stereocontrolled Total Synthesis of Lipoxin B4 and its Biological Activity as a Pro‐Resolving Lipid Mediator of Neuroinflammation","abstract":"Abstract Two stereocontrolled, efficient, and modular syntheses of eicosanoid lipoxin B4 (LXB 4 ) are reported. One features a stereoselective reduction followed by an asymmetric epoxidation sequence to set the vicinal diol stereocentres. The dienyne was installed via a one‐pot Wittig olefination and base‐mediated epoxide ring opening cascade. The other approach installed the diol through an asymmetric dihydroxylation reaction followed by a Horner‐Wadsworth‐Emmons olefination to afford the common dienyne intermediate. Finally, a Sonogashira coupling and an alkyne hydrosilylation/proto‐desilylation protocol furnished LXB 4 in 25 % overall yield in just 10 steps. For the first time, LXB 4 has been fully characterized spectroscopically with its structure confirmed as previously reported. We have demonstrated that the synthesized LXB 4 showed similar biological activity to commercial sources in a cellular neuroprotection model. This synthetic route can be employed to synthesize large quantities of LXB 4 , enable synthesis of new analogs, and chemical probes for receptor and pathway characterization.","journal":"Chemistry - A European Journal","year":2022,"id":271670,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":12,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9477,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2022-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":937558,"name":"Carla E. Brown","orcid":null,"position":1,"is_corresponding":false},{"id":937087,"name":"Alexander J. Nielsen","orcid":"0000-0003-0608-8771","position":2,"is_corresponding":false},{"id":937088,"name":"Changmo Kim","orcid":"0000-0001-9652-8675","position":3,"is_corresponding":false},{"id":431478,"name":"Izhar Livne‐Bar","orcid":null,"position":4,"is_corresponding":false},{"id":937089,"name":"Philip J. Parsons","orcid":"0000-0002-9158-4034","position":5,"is_corresponding":false},{"id":937559,"name":"Christophe Boldron","orcid":null,"position":6,"is_corresponding":false},{"id":937090,"name":"François Autelitano","orcid":"0000-0001-6269-2629","position":7,"is_corresponding":false},{"id":937091,"name":"Donald F. Weaver","orcid":"0000-0003-2042-6220","position":8,"is_corresponding":false},{"id":430733,"name":"Jeremy M. Sivak","orcid":"0000-0002-8776-223X","position":9,"is_corresponding":false},{"id":937092,"name":"Mark A. Reed","orcid":"0000-0002-0293-2691","position":10,"is_corresponding":false},{"id":937557,"name":"C. Frank Lee","orcid":null,"position":0,"is_corresponding":true}],"reference_count":78,"raw_metadata":null,"created_at":"2026-07-19T00:27:39.717534Z","pmid":"35491534","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}