{"doi":"10.1039/d3sc00651d","title":"Total synthesis of (−)-scabrolide A and (−)-yonarolide","abstract":"The complete account of the total syntheses of scabrolide A and yonarolide is disclosed. This article describes an initial approach involving a bio-inspired macrocyclization/transannular Diels-Alder cascade, which ultimately failed due to undesired reactivity during macrocycle construction. Next, the evolution of a second and third strategy, which both involve an initial intramolecular Diels-Alder reaction followed by a late-stage closure of the seven-membered ring of scabrolide A are detailed. The third strategy was first validated on a simplified system, but problems were encountered during a key [2 + 2] photocycloaddition on the fully elaborated system. An olefin protection strategy was employed to circumvent this problem, ultimately leading to the completion of the first total synthesis of scabrolide A and the closely related natural product yonarolide.","journal":"Chemical Science","year":2023,"id":336104,"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":19,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9456,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"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":1067047,"name":"Steven A. Loskot","orcid":null,"position":1,"is_corresponding":false},{"id":690271,"name":"Christopher E. Reimann","orcid":null,"position":2,"is_corresponding":false},{"id":1066505,"name":"Beau P. Pritchett","orcid":"0000-0001-9922-9160","position":3,"is_corresponding":false},{"id":706042,"name":"Scott C. Virgil","orcid":"0000-0001-8586-5641","position":4,"is_corresponding":false},{"id":239507,"name":"Brian M. Stoltz","orcid":"0000-0001-9837-1528","position":5,"is_corresponding":false},{"id":406406,"name":"Nicholas J. Hafeman","orcid":"0000-0001-7525-7597","position":0,"is_corresponding":true}],"reference_count":73,"raw_metadata":null,"created_at":"2026-07-19T01:10:17.243221Z","pmid":"37181769","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":[]}