{"doi":"10.1021/ja505131v","title":"Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core","abstract":null,"journal":"Journal of the American Chemical Society","year":2014,"id":650474,"datarank":0.5606504427425053,"base_score":3.7376696182833684,"endowment":3.7376696182833684,"self_citation_contribution":0.5606504427425053,"citation_network_contribution":0.0,"self_endowment_contribution":0.5606504427425053,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":41,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1696070,"name":"Carolyn S. Wei","orcid":null,"position":1,"is_corresponding":false},{"id":107935,"name":"Carrie E. Yozwiak","orcid":null,"position":2,"is_corresponding":false},{"id":1696071,"name":"Arash Soheili","orcid":null,"position":3,"is_corresponding":false},{"id":1696072,"name":"Sara O. Smithback","orcid":null,"position":4,"is_corresponding":false},{"id":1696073,"name":"James L. Leighton","orcid":null,"position":5,"is_corresponding":false},{"id":1696069,"name":"Christopher W. Plummer","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core","abstract":"An approach to the synthesis of the (iso)cyclocitrinol core structure is described. The key step is a tandem Ireland Claisen/Cope rearrangement sequence, wherein the Ireland Claisen rearrangement effects ring contraction to a strained 10-membered ring, and that strain in turn drives the Cope rearrangement under unusually mild thermal conditions. A major side product was identified as resulting from an unexpected and remarkably facile [1,3]-sigmatropic rearrangement, and a tactic to disfavor the [1,3] pathway and increase the efficiency of the tandem reaction was rationally devised.","is_dataset_classified":null,"base_score":3.7376696182833684,"endowment":3.7376696182833684,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"24967720","pmcid":null,"openalex_id":"https://openalex.org/W4232335403","authors":[],"funders":[{"funder_name":"Division of Chemistry","grant_id":"CHE-0619638","title":null}],"total_grants":1,"fwci":2.4365,"citation_percentile":0.88656941,"influential_citations":0,"citation_trend":[{"year":2014,"count":2},{"year":2015,"count":5},{"year":2016,"count":4},{"year":2017,"count":5},{"year":2018,"count":3},{"year":2019,"count":4},{"year":2020,"count":5},{"year":2021,"count":1},{"year":2022,"count":2},{"year":2023,"count":2},{"year":2024,"count":3},{"year":2025,"count":2},{"year":2026,"count":3}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://pubs.acs.org/doi/pdf/10.1021/ja505131v","host_type":"publisher"},{"url":"https://doi.org/10.1021/ja505131v","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/24967720","host_type":"repository"}],"fields_of_study":["Synthetic Organic Chemistry Methods","Traditional and Medicinal Uses of Annonaceae","Carbohydrate Chemistry and Synthesis","Lactones","Models, Molecular","Molecular Conformation","Stereoisomerism","Terpenes"],"mesh_terms":["Lactones","Models, Molecular","Molecular Conformation","Stereoisomerism","Terpenes"],"keywords":["Chemistry","Sigmatropic reaction","Cope rearrangement","Tandem","Claisen rearrangement","Carroll rearrangement","Ring strain","Rearrangement reaction","Combinatorial chemistry","Stereochemistry","Core (optical fiber)","Ring (chemistry)","Organic chemistry","Catalysis"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-10T05:32:46.226240Z","pmid":null,"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":[]}