{"doi":"10.1021/jacs.2c08803","title":"Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides","abstract":"Detailed herein are our synthetic studies toward the preparation of the C18- and C19-benzenoid cephalotane-type norditerpenoids. Guided by chemical network analysis, the core structure of this natural product family was constructed in a concise manner using an iterative cross-coupling, followed by a formal inverse-electron-demand [4 + 2] cycloaddition. Initial efforts to functionalize an alkene group in the [4 + 2] cycloadduct using a Mukaiyama hydration and a subsequent olefination led to the complete C18-carbon framework. While effective, this approach proved lengthy and prompted the development of a direct alkene difunctionalization that relies on borocupration to advance the cycloadduct to the natural products. Late-stage peripheral C–H functionalization facilitated access to all of the known cephanolides in 6–10 steps as well as five recently isolated ceforalides in 8–13 steps.","journal":"Journal of the American Chemical Society","year":2022,"id":238007,"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":57,"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":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":495631,"name":"Kristen E. Gardner","orcid":"0000-0002-6712-7001","position":1,"is_corresponding":false},{"id":861464,"name":"Stefan Wiesler","orcid":"0000-0002-4302-7639","position":2,"is_corresponding":false},{"id":640293,"name":"Maximilian Haider","orcid":"0000-0002-4712-8832","position":3,"is_corresponding":false},{"id":640295,"name":"Alina Eggert","orcid":"0000-0001-6451-8931","position":4,"is_corresponding":false},{"id":308347,"name":"Richmond Sarpong","orcid":"0000-0002-0028-6323","position":5,"is_corresponding":false},{"id":640294,"name":"Goh Sennari","orcid":"0000-0003-4347-7522","position":0,"is_corresponding":true}],"reference_count":87,"raw_metadata":null,"created_at":"2026-07-19T00:22:26.932537Z","pmid":"36198090","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":[]}