{"doi":"10.1002/ejoc.201801780","title":"High‐Yielding Diastereoselective <i>syn</i>‐Dihydroxylation of Protected HBO: An Access to D‐(+)‐Ribono‐1,4‐lactone and 5‐<i>O</i>‐Protected Analogues","abstract":"<jats:p>A diastereoselective chemoenzymatic synthetic pathway to D‐(+)‐ribono‐1,4‐lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose‐based levoglucosenone (<jats:bold>LGO</jats:bold>). This route involves a sustainable Baeyer‐Villiger oxidation of <jats:bold>LGO</jats:bold> to produce enantiopure (S)‐γ‐hydroxymethyl‐α,β‐butenolide (<jats:bold>HBO</jats:bold>) that is further functionalized with various protecting groups to provide 5‐<jats:italic>O</jats:italic>‐protected γ‐hydroxymethyl‐α,β‐butenolides. The latter then undergo a diastereoselective and high‐yielding <jats:italic>syn</jats:italic>‐dihydroxylation of the α,β‐unsaturated lactone moiety followed by a deprotection step to give D‐(+)‐ribono‐1,4‐lactone. Through this 4‐step synthetic route from <jats:bold>LGO</jats:bold>, D‐(+)‐ribono‐1,4‐lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5‐<jats:italic>O</jats:italic>‐<jats:italic>tert</jats:italic>‐butyldimethylsilyl‐, 5‐<jats:italic>O</jats:italic>‐<jats:italic>tert</jats:italic>‐butyldiphenylsilyl‐ as well as 5‐<jats:italic>O</jats:italic>‐benzyl‐ribono‐1,4‐lactones are obtained in 3 steps from <jats:bold>LGO</jats:bold> in 58, 61 and 40 %, respectively.</jats:p>","journal":"European Journal of Organic Chemistry","year":2019,"id":687610,"datarank":0.41588830833596724,"base_score":2.772588722239781,"endowment":2.772588722239781,"self_citation_contribution":0.41588830833596724,"citation_network_contribution":0.0,"self_endowment_contribution":0.41588830833596724,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":15,"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":1796356,"name":"Guillaume Bonneau","orcid":null,"position":1,"is_corresponding":false},{"id":1796357,"name":"Aurélien Peru","orcid":null,"position":2,"is_corresponding":false},{"id":1796358,"name":"Fanny Brunissen","orcid":null,"position":3,"is_corresponding":false},{"id":1796360,"name":"Marine Janvier","orcid":null,"position":4,"is_corresponding":false},{"id":1796361,"name":"Arnaud Haudrechy","orcid":null,"position":5,"is_corresponding":false},{"id":1424113,"name":"Florent Allais","orcid":"0000-0003-4132-6210","position":6,"is_corresponding":false},{"id":1796355,"name":"Maxime Moreaux","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"High‐Yielding Diastereoselective <i>syn</i>‐Dihydroxylation of Protected HBO: An Access to D‐(+)‐Ribono‐1,4‐lactone and 5‐<i>O</i>‐Protected Analogues","abstract":"<jats:p>A diastereoselective chemoenzymatic synthetic pathway to D‐(+)‐ribono‐1,4‐lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose‐based levoglucosenone (<jats:bold>LGO</jats:bold>). This route involves a sustainable Baeyer‐Villiger oxidation of <jats:bold>LGO</jats:bold> to produce enantiopure (S)‐γ‐hydroxymethyl‐α,β‐butenolide (<jats:bold>HBO</jats:bold>) that is further functionalized with various protecting groups to provide 5‐<jats:italic>O</jats:italic>‐protected γ‐hydroxymethyl‐α,β‐butenolides. The latter then undergo a diastereoselective and high‐yielding <jats:italic>syn</jats:italic>‐dihydroxylation of the α,β‐unsaturated lactone moiety followed by a deprotection step to give D‐(+)‐ribono‐1,4‐lactone. Through this 4‐step synthetic route from <jats:bold>LGO</jats:bold>, D‐(+)‐ribono‐1,4‐lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5‐<jats:italic>O</jats:italic>‐<jats:italic>tert</jats:italic>‐butyldimethylsilyl‐, 5‐<jats:italic>O</jats:italic>‐<jats:italic>tert</jats:italic>‐butyldiphenylsilyl‐ as well as 5‐<jats:italic>O</jats:italic>‐benzyl‐ribono‐1,4‐lactones are obtained in 3 steps from <jats:bold>LGO</jats:bold> in 58, 61 and 40 %, respectively.</jats:p>","is_dataset_classified":null,"base_score":2.772588722239781,"endowment":2.772588722239781,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"21097893","pmcid":null,"openalex_id":"https://openalex.org/W2902553376","authors":[],"funders":[],"total_grants":0,"fwci":0.4614,"citation_percentile":0.59367969,"influential_citations":0,"citation_trend":[{"year":2019,"count":3},{"year":2020,"count":2},{"year":2022,"count":3},{"year":2023,"count":1},{"year":2024,"count":2},{"year":2025,"count":2},{"year":2026,"count":2}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201801780","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.201801780","host_type":"publisher"},{"url":"https://doi.org/10.1002/ejoc.201801780","host_type":"journal"},{"url":"https://hal.science/hal-02052678","host_type":"repository"}],"fields_of_study":["Catalysis for Biomass Conversion","Biofuel production and bioconversion","Carbohydrate Chemistry and Synthesis"],"mesh_terms":[],"keywords":["Chemistry","Dihydroxylation","Lactone","Enantiopure drug","Butenolide","Hydroxymethyl","Stereochemistry","Moiety","Protecting group","Enantioselective synthesis","Organic chemistry","Catalysis"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Responsible consumption and production"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-18T22:20:28.453981Z","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":[]}