{"doi":"10.1039/d4ra07318e","title":"Efficient convergent synthesis of 1,3-diazepinone nucleosides by ring-closing metathesis and direct glycosylation","abstract":"A new and highly efficient ring-closing metathesis-based strategy was developed for the synthesis of the cyclic urea 1,3-diazepinone, presenting significant improvement upon previous methods. Using a direct glycosylation approach, analogues of the potent cytidine deaminase (CDA) inhibitor diazepinone riboside were then synthesized including 2'-deoxyribo-, 2'-deoxy-2'-fluoroarabino-, and 2'-deoxy-2',2'-difluoro-diazepinone nucleosides, all with moderate to good yield and excellent anomeric selectivity. Crucially, in contrast to the previous multistep linear synthesis of 2'-deoxyribo- and 2'-deoxy-2'-fluoroarabino-diazepinone nucleosides, this is the first report of direct glycosylation to access these nucleosides. Overall, we report efficient convergent routes to multiple 2'-modified-diazepinone nucleosides for further evaluation as CDA and potential APOBEC3 inhibitors.","journal":"RSC Advances","year":2024,"id":506405,"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":0,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9498,"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":1357611,"name":"Jonathan Findell","orcid":"0009-0005-4011-0903","position":1,"is_corresponding":false},{"id":1357612,"name":"Dinesh S. Barak","orcid":"0000-0002-8536-8546","position":2,"is_corresponding":false},{"id":249895,"name":"Celia A. Schiffer","orcid":"0000-0003-2270-6613","position":3,"is_corresponding":false},{"id":348431,"name":"Jonathan K. Watts","orcid":"0000-0001-5706-1734","position":4,"is_corresponding":false},{"id":524168,"name":"Akbar Ali","orcid":"0000-0003-3491-791X","position":5,"is_corresponding":false},{"id":348430,"name":"Adam K. Hedger","orcid":"0000-0003-1529-2598","position":0,"is_corresponding":true}],"reference_count":29,"raw_metadata":null,"created_at":"2026-07-19T02:10:54.646711Z","pmid":"39569122","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":[]}