{"doi":"10.1021/jo1001559","title":"Synthesis of Dihydroplakortin, 6-<i>epi</i>-Dihydroplakortin, and Their C10-Desethyl Analogues","abstract":null,"journal":"The Journal of Organic Chemistry","year":2010,"id":690062,"datarank":0.5806801516361837,"base_score":3.8712010109078907,"endowment":3.8712010109078907,"self_citation_contribution":0.5806801516361837,"citation_network_contribution":0.0,"self_endowment_contribution":0.5806801516361837,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":47,"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":1802768,"name":"Emanuele Gabellieri","orcid":null,"position":1,"is_corresponding":false},{"id":1802769,"name":"Salvatore Sanna Coccone","orcid":null,"position":2,"is_corresponding":false},{"id":373470,"name":"Francesc Martí","orcid":"0000-0002-2066-6884","position":3,"is_corresponding":false},{"id":1802770,"name":"Orazio Taglialatela-Scafati","orcid":null,"position":4,"is_corresponding":false},{"id":114883,"name":"Ettore Novellino","orcid":null,"position":5,"is_corresponding":false},{"id":463150,"name":"Giuseppe Campiani","orcid":"0000-0001-5295-9529","position":6,"is_corresponding":false},{"id":463149,"name":"Stefania Butini","orcid":"0000-0002-8471-0880","position":7,"is_corresponding":false},{"id":463148,"name":"Sandra Gemma","orcid":"0000-0002-8313-2417","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Synthesis of Dihydroplakortin, 6-<i>epi</i>-Dihydroplakortin, and Their C10-Desethyl Analogues","abstract":"The first synthesis of the marine endoperoxide 9,10-dihydroplakortin, of its C10-desethyl analogue, and of their corresponding C6 epimers is described. Stereogenic centers at C4 and at the lateral chain have been stereoselectively synthesized through Evans' chiral auxiliary chemistry. Moreover, the reported synthesis features a one-pot three-step hydroperoxysilylation/cyclization reaction for the construction of the endoperoxide ring system. Homologation of the aldehyde resulting from diol cleavage through a Wittig-based strategy gave access to the ester-containing lateral chain at C3.","is_dataset_classified":null,"base_score":3.8712010109078907,"endowment":3.8712010109078907,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"20199093","pmcid":null,"openalex_id":"https://openalex.org/W2024445010","authors":[],"funders":[],"total_grants":0,"fwci":4.6429,"citation_percentile":0.93910848,"influential_citations":0,"citation_trend":[{"year":2012,"count":6},{"year":2013,"count":4},{"year":2014,"count":8},{"year":2015,"count":2},{"year":2016,"count":4},{"year":2017,"count":3},{"year":2018,"count":2},{"year":2019,"count":3},{"year":2020,"count":3},{"year":2021,"count":3},{"year":2022,"count":1},{"year":2023,"count":1},{"year":2024,"count":1}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://pubs.acs.org/doi/pdf/10.1021/jo1001559","host_type":"publisher"},{"url":"https://doi.org/10.1021/jo1001559","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/20199093","host_type":"repository"},{"url":"http://hdl.handle.net/11365/2837","host_type":"repository"}],"fields_of_study":["Marine Sponges and Natural Products","Asymmetric Synthesis and Catalysis","Sesquiterpenes and Asteraceae Studies","Medicine","Chemistry","Aldehydes","Combinatorial Chemistry Techniques","Cyclization","Epoxy Compounds","Marine Toxins","Molecular Structure","Nuclear Magnetic Resonance, Biomolecular","Peroxides","Stereoisomerism"],"mesh_terms":["Aldehydes","Cyclization","Epoxy Compounds","Marine Toxins","Peroxides","Stereoisomerism","Molecular Structure","Nuclear Magnetic Resonance, Biomolecular","Combinatorial Chemistry Techniques"],"keywords":["Stereocenter","Chemistry","Epimer","Aldehyde","Stereochemistry","Wittig reaction","Diol","Cleavage (geology)","Chemical synthesis","Ring (chemistry)","Enantioselective synthesis","Organic chemistry","In vitro","Biochemistry","Catalysis"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Life below water"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-22T21:51:02.918228Z","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":[]}