{"doi":"10.1021/jacs.3c04493","title":"Enantioselective Total Synthesis of (−)-Caulamidine A","abstract":"Marine bryozoans continue to provide architecturally fascinating halogenated alkaloids that pose unique challenges for chemical synthesis. The antimalarial alkaloids caulamidines A and B, recently isolated from Caulibugula intermis, contain an intricate bis-amidine core and a chlorine-bearing neopentylic stereocenter. Compared to topologically similar C 20 bis(cyclotryptamine) alkaloids, caulamidines possess an additional carbon atom of unknown biosynthetic origins, which renders their entire skeleton nonsymmetric and nondimeric. Herein, we report the first total synthesis of caulamidine A and confirm its absolute configuration. Key chemical findings include the exploitation of glycol bistriflate to facilitate a rapid, diastereoselective ketone-amidine annulation reaction and a highly diastereoselective hydrogen atom transfer to correctly establish the key chlorine-bearing stereogenic center.","journal":"Journal of the American Chemical Society","year":2023,"id":329226,"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":20,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9488,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2023-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":263054,"name":"Thomas J. Maimone","orcid":"0000-0001-5823-692X","position":1,"is_corresponding":false},{"id":1051838,"name":"Zhouyang Zhu","orcid":"0009-0001-1938-6586","position":0,"is_corresponding":true}],"reference_count":44,"raw_metadata":null,"created_at":"2026-07-19T01:09:01.509601Z","pmid":"37343162","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":[]}