{"doi":"10.1021/jacs.2c10272","title":"General Synthetic Approach to Diverse Taxane Cores","abstract":"Chemical synthesis of natural products is typically inspired by the structure and function of a target molecule. When both factors are of interest, such as in the case of taxane diterpenoids, a synthesis can both serve as a platform for synthetic strategy development and enable new biological exploration. Guided by this paradigm, we present here a unified enantiospecific approach to diverse taxane cores from the feedstock monoterpenoid (S)-carvone. Key to the success of our approach was the use of a skeletal remodeling strategy which began with the divergent reorganization and convergent coupling of two carvone-derived fragments, facilitated by Pd-catalyzed C–C bond cleavage tactics. This coupling was followed by additional restructuring using a Sm(II)-mediated rearrangement and a bioinspired, visible-light induced, transannular [2 + 2] photocycloaddition. Overall, this divergent monoterpenoid remodeling/convergent fragment coupling approach to complex diterpenoid synthesis provides access to structurally disparate taxane cores which have set the stage for the preparation of a wide range of taxanes.","journal":"Journal of the American Chemical Society","year":2022,"id":251479,"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":25,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9497,"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":411994,"name":"Brian Wang","orcid":"0000-0002-5903-4593","position":1,"is_corresponding":false},{"id":895450,"name":"Benjamin C. Wyler","orcid":null,"position":2,"is_corresponding":false},{"id":308341,"name":"Jin Su Ham","orcid":"0000-0003-0327-7139","position":3,"is_corresponding":false},{"id":895451,"name":"Nicholas R. O’Connor","orcid":null,"position":4,"is_corresponding":false},{"id":894811,"name":"Shota Nagasawa","orcid":"0000-0002-9207-4423","position":5,"is_corresponding":false},{"id":894812,"name":"Yuto Kimura","orcid":"0000-0001-6848-3887","position":6,"is_corresponding":false},{"id":894813,"name":"Carolin Manske","orcid":"0000-0002-1079-7944","position":7,"is_corresponding":false},{"id":895452,"name":"Maximilian Scherübl","orcid":null,"position":8,"is_corresponding":false},{"id":786029,"name":"Johny M. Nguyen","orcid":"0000-0001-7044-9127","position":9,"is_corresponding":false},{"id":308347,"name":"Richmond Sarpong","orcid":"0000-0002-0028-6323","position":10,"is_corresponding":false},{"id":495630,"name":"Melecio A. Perea","orcid":"0000-0002-4112-6916","position":0,"is_corresponding":true}],"reference_count":63,"raw_metadata":null,"created_at":"2026-07-19T00:24:41.993282Z","pmid":"36346461","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":[]}