{"id":"https://openalex.org/W4407762017","doi":"https://doi.org/10.1021/acs.joc.4c03173","title":"Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid","display_name":"Stereoselective Synthesis of (R)-all-trans-13,14-Dihydroretinol and -Retinoic Acid","publication_year":2025,"publication_date":"2025-02-20","ids":{"openalex":"https://openalex.org/W4407762017","doi":"https://doi.org/10.1021/acs.joc.4c03173","pmid":"https://pubmed.ncbi.nlm.nih.gov/39977339","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/11894646"},"language":"ru","primary_location":{"id":"doi:10.1021/acs.joc.4c03173","doi":"https://doi.org/10.1021/acs.joc.4c03173","is_oa":true,"landing_page_url":"https://doi.org/10.1021/acs.joc.4c03173","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://doi.org/10.1021/acs.joc.4c03173","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5016533279","display_name":"Paul Wienecke","orcid":"https://orcid.org/0000-0002-3085-0642","observed_orcids":["https://orcid.org/0000-0002-3085-0642"]},"institutions":[{"id":"https://openalex.org/I169381384","display_name":"University of Groningen","ror":"https://ror.org/012p63287","country_code":"NL","type":"education","lineage":["https://openalex.org/I169381384"]}],"countries":["NL"],"is_corresponding":true,"raw_author_name":"Paul Wienecke","raw_affiliation_strings":["Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands"],"raw_orcid":"https://orcid.org/0000-0002-3085-0642","affiliations":[{"raw_affiliation_string":"Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands","institution_ids":["https://openalex.org/I169381384"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5051792983","display_name":"Adriaan J. Minnaard","orcid":"https://orcid.org/0000-0002-5966-1300","observed_orcids":["https://orcid.org/0000-0002-5966-1300"]},"institutions":[{"id":"https://openalex.org/I169381384","display_name":"University of Groningen","ror":"https://ror.org/012p63287","country_code":"NL","type":"education","lineage":["https://openalex.org/I169381384"]}],"countries":["NL"],"is_corresponding":true,"raw_author_name":"Adriaan J. Minnaard","raw_affiliation_strings":["Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands"],"raw_orcid":"https://orcid.org/0000-0002-5966-1300","affiliations":[{"raw_affiliation_string":"Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands","institution_ids":["https://openalex.org/I169381384"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5016533279","https://openalex.org/A5051792983"],"corresponding_institution_ids":["https://openalex.org/I169381384"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":{"value":4500,"currency":"USD","value_usd":4500},"fwci":0.6012,"has_fulltext":false,"cited_by_count":2,"citation_normalized_percentile":{"value":0.57317781,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":96,"max":97},"biblio":{"volume":"90","issue":"9","first_page":"3512","last_page":"3518"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11559","display_name":"Retinoids in leukemia and cellular processes","score":0.6625999808311462,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T11559","display_name":"Retinoids in leukemia and cellular processes","score":0.6625999808311462,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.09730000048875809,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13239","display_name":"Phosphorus compounds and reactions","score":0.0771000012755394,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/vitamin-a-metabolites","display_name":"vitamin A metabolites","score":0.9760000109672546},{"id":"https://openalex.org/keywords/stereoselective-total-synthesis","display_name":"stereoselective total synthesis","score":0.9319999814033508},{"id":"https://openalex.org/keywords/all-trans-retinol","display_name":"all-trans-retinol","score":0.6940000057220459}],"concepts":[{"id":"https://openalex.org/C2781121885","wikidata":"https://www.wikidata.org/wiki/Q425517","display_name":"Retinoic acid","level":3,"score":0.7559278011322021},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.7099695205688477},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.41860708594322205},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4031144976615906},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.12875080108642578},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","level":2,"score":0.053597211837768555},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[],"locations_count":5,"locations":[{"id":"doi:10.1021/acs.joc.4c03173","doi":"https://doi.org/10.1021/acs.joc.4c03173","is_oa":true,"landing_page_url":"https://doi.org/10.1021/acs.joc.4c03173","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmh:oai:europepmc.org:10706811","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11894646","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":null,"raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:11894646","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11894646","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"J Org Chem","raw_type":"Text"},{"id":"pmid:39977339","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/39977339","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of organic chemistry","raw_type":"Journal Article"},{"id":"pmh:oai:pure.rug.nl:openaire/bb7281cb-1df8-4912-a7dd-7d0ba0027623","doi":null,"is_oa":true,"landing_page_url":"https://hdl.handle.net/11370/bb7281cb-1df8-4912-a7dd-7d0ba0027623","pdf_url":null,"source":{"id":"https://openalex.org/S4306400420","display_name":"University of Groningen research database (University of Groningen / Centre for Information Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I169381384","host_organization_name":"University of Groningen","host_organization_lineage":["https://openalex.org/I169381384"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Wienecke, P & Minnaard, A J 2025, 'Stereoselective Synthesis of ( R )-all- trans -13,14-Dihydroretinol and -Retinoic Acid.', The Journal of Organic Chemistry, vol. 90, no. 9, 4c03173, pp. 3512\u20133518. https://doi.org/10.1021/acs.joc.4c03173","raw_type":"info:eu-repo/semantics/article"}],"best_oa_location":{"id":"doi:10.1021/acs.joc.4c03173","doi":"https://doi.org/10.1021/acs.joc.4c03173","is_oa":true,"landing_page_url":"https://doi.org/10.1021/acs.joc.4c03173","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"sustainable_development_goals":[{"id":"https://metadata.un.org/sdg/3","score":0.4043000042438507,"display_name":"Good health and well-being"}],"study_designs":[],"awards":[{"id":"https://openalex.org/G9000877944","display_name":"Metabolic determinants of Mtb virulence, vulnerability and variation","funder_award_id":"U19AI162584","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"}],"funders":[{"id":"https://openalex.org/F4320337355","display_name":"National Institute of Allergy and Infectious Diseases","ror":"https://ror.org/043z4tv69"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":30,"referenced_works":["https://openalex.org/W1966185846","https://openalex.org/W1968222382","https://openalex.org/W1968479888","https://openalex.org/W2008245372","https://openalex.org/W2011707142","https://openalex.org/W2017449375","https://openalex.org/W2018108924","https://openalex.org/W2021492604","https://openalex.org/W2027564443","https://openalex.org/W2034434182","https://openalex.org/W2047433340","https://openalex.org/W2063713352","https://openalex.org/W2071732510","https://openalex.org/W2083001201","https://openalex.org/W2121802938","https://openalex.org/W2122581088","https://openalex.org/W2122662309","https://openalex.org/W2129555503","https://openalex.org/W2139430168","https://openalex.org/W2143035222","https://openalex.org/W2150861118","https://openalex.org/W2345680076","https://openalex.org/W2754426827","https://openalex.org/W2952153270","https://openalex.org/W2953056359","https://openalex.org/W3018024714","https://openalex.org/W3080918973","https://openalex.org/W4220978255","https://openalex.org/W4231682268","https://openalex.org/W4391933785"],"related_works":["https://openalex.org/W2020297909","https://openalex.org/W1966185846","https://openalex.org/W2792765017","https://openalex.org/W1984986959","https://openalex.org/W179305143","https://openalex.org/W1968222382","https://openalex.org/W2953021339","https://openalex.org/W4255368028","https://openalex.org/W1970521366","https://openalex.org/W2337872855"],"abstract_inverted_index":{"High":[0],"Resolution":[1],"Image":[2],"Download":[3],"MS":[4],"PowerPoint":[5],"Slide":[6],"Vitamin":[7],"A":[8,48],"(or":[9],"all-":[10],"trans":[11,53],"-retinol)":[12],"metabolites":[13,49],"are":[14],"involved":[15],"in":[16],"a":[17,41,65],"wide":[18],"range":[19],"of":[20,26,45],"cellular":[21],"processes.":[22],"However,":[23],"the":[24,46,75],"investigation":[25],"their":[27,34],"biological":[28],"role":[29],"is":[30],"hampered":[31],"due":[32],"to":[33],"very":[35],"limited":[36],"availability.":[37],"Herein":[38],"we":[39],"report":[40],"stereoselective":[42],"total":[43],"synthesis":[44],"vitamin":[47],"(":[50],"R":[51],")-all-":[52],"-13,14-dihydroretinol":[54],"and":[55,64],"-retinoic":[56],"acid,":[57],"applying":[58],"an":[59],"E":[60],"-selective":[61],"HWE":[62],"olefination":[63],"Ru(II)":[66],"catalyzed":[67],"intramolecular":[68],"7-":[69],"endo":[70],"-":[71],"dig":[72],"hydrosilylation":[73],"as":[74],"key":[76],"steps.":[77]},"counts_by_year":[{"year":2026,"cited_by_count":2}],"updated_date":"2026-10-28T10:33:24.094632","created_date":"2025-02-20T00:00:00"}
