{"doi":"10.3762/bjoc.20.115","title":"Computation-guided scaffold exploration of 2<i>E</i>,6<i>E</i>-1,10-<i>trans/cis-</i>eunicellanes","abstract":"Eunicellane diterpenoids are a unique family of natural products containing a foundational 6/10-bicyclic framework and can be divided into two main classes, cis and trans , based on the configurations of their ring fusion at C1 and C10. Previous studies on two bacterial diterpene synthases, Bnd4 and AlbS, revealed that these enzymes form cis - and trans -eunicellane skeletons, respectively. Although the structures of these diterpenes only differed in their configuration at a single position, C1, they displayed distinct chemical and thermal reactivities. Here, we used a combination of quantum chemical calculations and chemical transformations to probe their intrinsic properties, which result in protonation-initiated cyclization, Cope rearrangement, and atropisomerism. Finally, we exploited the reactivity of the trans -eunicellane skeleton to generate a series of 6/6/6 gersemiane-type diterpenes via electrophilic cyclization.","journal":"Beilstein Journal of Organic Chemistry","year":2024,"id":459638,"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":4,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9598,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1286726,"name":"Sana Jindani","orcid":"0000-0002-5224-6198","position":1,"is_corresponding":false},{"id":464977,"name":"Volga Kojasoy","orcid":"0000-0003-4832-0479","position":2,"is_corresponding":false},{"id":1034978,"name":"Teresa Ortega","orcid":"0000-0003-0486-6904","position":3,"is_corresponding":false},{"id":1264843,"name":"Erin M Marshall","orcid":"0009-0000-0681-0600","position":4,"is_corresponding":false},{"id":1287175,"name":"Khalil A Abboud","orcid":null,"position":5,"is_corresponding":false},{"id":588267,"name":"Sandra Loesgen","orcid":"0000-0003-1090-564X","position":6,"is_corresponding":false},{"id":389027,"name":"Dean J. Tantillo","orcid":"0000-0002-2992-8844","position":7,"is_corresponding":false},{"id":568959,"name":"Jeffrey D. Rudolf","orcid":"0000-0003-2718-9651","position":8,"is_corresponding":false},{"id":711099,"name":"Zining Li","orcid":"0000-0002-6921-8417","position":0,"is_corresponding":true}],"reference_count":22,"raw_metadata":null,"created_at":"2026-07-19T02:03:59.428859Z","pmid":"38887579","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":[]}