{"doi":"10.1021/acs.joc.5c02804","title":"A Concise Route to Orthogonally Protected Bulgecinine","abstract":"Bulgecinine is the core structure for inhibitors of the important lytic transglycosylases of bacterial cell-envelope homeostasis. Their central pyrrolidine ring mimics, as the protonated amine, the transient oxocarbenium species of the enzymatic reaction. We report a concise synthesis of protected bulgecinine 9 (nine linear steps and 12% overall yield). The key step is the vinyl Grignard addition to a nitrone (pyrrolidine- N -oxide) intermediate. Compound 9 possesses the correct absolute stereochemistry of the three stereogenic centers, validated by an X-ray structure.","journal":"The Journal of Organic Chemistry","year":2025,"id":586896,"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":0,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9491,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2025-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1501319,"name":"Pradip Shit","orcid":"0000-0002-0716-5356","position":1,"is_corresponding":false},{"id":493603,"name":"Van Trung Nguyen","orcid":"0000-0003-3070-7683","position":2,"is_corresponding":false},{"id":799189,"name":"Allen G. Oliver","orcid":"0000-0002-0511-1127","position":3,"is_corresponding":false},{"id":739838,"name":"Jed F. Fisher","orcid":"0000-0002-7174-4352","position":4,"is_corresponding":false},{"id":364759,"name":"Shahriar Mobashery","orcid":"0000-0002-7695-7883","position":5,"is_corresponding":false},{"id":34684,"name":"Qiuyun Yang","orcid":"0009-0009-2842-7974","position":0,"is_corresponding":true}],"reference_count":23,"raw_metadata":null,"created_at":"2026-07-19T02:59:32.191237Z","pmid":"41432171","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":[]}