{"doi":"10.1126/science.ade0032","title":"Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene","abstract":"Small rings that contain allenes are unconventional transient compounds that have been known since the 1960s. Despite being discovered around the same time as benzyne and offering a number of synthetically advantageous features, strained cyclic allenes have seen relatively little use in chemical synthesis. We report a concise total synthesis of the manzamine alkaloid lissodendoric acid A, which hinges on the development of a regioselective, diastereoselective, and stereospecific trapping of a fleeting cyclic allene intermediate. This key step swiftly assembles the azadecalin framework of the natural product, allows for a succinct synthetic endgame, and enables a 12-step total synthesis (longest linear sequence; 0.8% overall yield). These studies demonstrate that strained cyclic allenes are versatile building blocks in chemical synthesis.","journal":"Science","year":2023,"id":319428,"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":55,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9518,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2023-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1028312,"name":"Nathan J. Adamson","orcid":"0000-0002-0872-0593","position":1,"is_corresponding":false},{"id":411279,"name":"Laura G. Wonilowicz","orcid":"0000-0001-8503-6835","position":2,"is_corresponding":false},{"id":912268,"name":"Daniel J. Nasrallah","orcid":"0000-0001-8010-6953","position":3,"is_corresponding":false},{"id":702106,"name":"Evan R. Darzi","orcid":"0000-0002-6900-2229","position":4,"is_corresponding":false},{"id":702107,"name":"Joyann S. Donaldson","orcid":"0000-0001-8873-0304","position":5,"is_corresponding":false},{"id":685230,"name":"Neil K. Garg","orcid":"0000-0002-7793-2629","position":6,"is_corresponding":false},{"id":685229,"name":"Francesca M. Ippoliti","orcid":"0000-0003-4655-0545","position":0,"is_corresponding":true}],"reference_count":51,"raw_metadata":null,"created_at":"2026-07-19T01:07:12.004111Z","pmid":"36656952","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":[]}