{"id":"https://openalex.org/W2950182785","doi":"https://doi.org/10.1021/jo040215h","title":"Synthesis of 4\u2018-Methyl and 4\u2018-Cyano Carbocyclic 2\u2018,3\u2018-Didehydro Nucleoside Analogues via 1,4-Addition to Substituted Cyclopentenones","display_name":"Synthesis of 4\u2018-Methyl and 4\u2018-Cyano Carbocyclic 2\u2018,3\u2018-Didehydro Nucleoside Analogues via 1,4-Addition to Substituted Cyclopentenones","publication_year":2004,"publication_date":"2004-10-30","ids":{"openalex":"https://openalex.org/W2950182785","doi":"https://doi.org/10.1021/jo040215h","mag":"2950182785","pmid":"https://pubmed.ncbi.nlm.nih.gov/15549827"},"language":"en","primary_location":{"id":"doi:10.1021/jo040215h","doi":"https://doi.org/10.1021/jo040215h","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo040215h","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":null,"license_id":null,"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":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5108393267","display_name":"Louis S. Hegedus","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I92446798","display_name":"Colorado State University","ror":"https://ror.org/03k1gpj17","country_code":"US","type":"education","lineage":["https://openalex.org/I92446798"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Louis S. Hegedus","raw_affiliation_strings":["Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 louis.hegedus@colostate.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 louis.hegedus@colostate.edu","institution_ids":["https://openalex.org/I92446798"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5091800759","display_name":"Jeff Cross","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I92446798","display_name":"Colorado State University","ror":"https://ror.org/03k1gpj17","country_code":"US","type":"education","lineage":["https://openalex.org/I92446798"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jeff Cross","raw_affiliation_strings":["Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 louis.hegedus@colostate.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 louis.hegedus@colostate.edu","institution_ids":["https://openalex.org/I92446798"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I92446798"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.4751,"has_fulltext":false,"cited_by_count":13,"citation_normalized_percentile":{"value":0.82354452,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":96},"biblio":{"volume":"69","issue":"24","first_page":"8492","last_page":"8495"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10526","display_name":"HIV/AIDS drug development and treatment","score":0.6894999742507935,"subfield":{"id":"https://openalex.org/subfields/2725","display_name":"Infectious Diseases"},"field":{"id":"https://openalex.org/fields/27","display_name":"Medicine"},"domain":{"id":"https://openalex.org/domains/4","display_name":"Health Sciences"}},"topics":[{"id":"https://openalex.org/T10526","display_name":"HIV/AIDS drug development and treatment","score":0.6894999742507935,"subfield":{"id":"https://openalex.org/subfields/2725","display_name":"Infectious Diseases"},"field":{"id":"https://openalex.org/fields/27","display_name":"Medicine"},"domain":{"id":"https://openalex.org/domains/4","display_name":"Health Sciences"}},{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.09589999914169312,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.03970000147819519,"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/nucleoside-analogs","display_name":"nucleoside analogues","score":0.8600000143051147},{"id":"https://openalex.org/keywords/carbocyclic-nucleosides","display_name":"carbocyclic nucleosides","score":0.9139999747276306},{"id":"https://openalex.org/keywords/conjugate-addition","display_name":"conjugate addition","score":0.8849999904632568},{"id":"https://openalex.org/keywords/cyclopentenones","display_name":"cyclopentenones","score":0.9110000133514404},{"id":"https://openalex.org/keywords/michael-addition","display_name":"Michael addition","score":0.8180000185966492},{"id":"https://openalex.org/keywords/epimerization","display_name":"epimerization","score":0.847000002861023},{"id":"https://openalex.org/keywords/nucleoside-synthesis","display_name":"nucleoside synthesis","score":0.609000027179718}],"concepts":[{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.8542118072509766},{"id":"https://openalex.org/C203130289","wikidata":"https://www.wikidata.org/wiki/Q926272","display_name":"Epimer","level":2,"score":0.8190948963165283},{"id":"https://openalex.org/C2776543447","wikidata":"https://www.wikidata.org/wiki/Q28734","display_name":"Nucleoside","level":2,"score":0.7479439973831177},{"id":"https://openalex.org/C2778689049","wikidata":"https://www.wikidata.org/wiki/Q898422","display_name":"Substituent","level":2,"score":0.7459322810173035},{"id":"https://openalex.org/C120095180","wikidata":"https://www.wikidata.org/wiki/Q2695010","display_name":"Allylic rearrangement","level":3,"score":0.6745948195457458},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6423047780990601},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5400797128677368},{"id":"https://openalex.org/C111185830","wikidata":"https://www.wikidata.org/wiki/Q503396","display_name":"Substitution reaction","level":2,"score":0.4693124294281006},{"id":"https://openalex.org/C2778220771","wikidata":"https://www.wikidata.org/wiki/Q1522579","display_name":"Substitution (logic)","level":2,"score":0.4624820649623871},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.32152947783470154},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2465420365333557},{"id":"https://openalex.org/C138885662","wikidata":"https://www.wikidata.org/wiki/Q5891","display_name":"Philosophy","level":0,"score":0.0678715705871582},{"id":"https://openalex.org/C41895202","wikidata":"https://www.wikidata.org/wiki/Q8162","display_name":"Linguistics","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D003500","descriptor_name":"Cyclization","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003517","descriptor_name":"Cyclopentanes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D009705","descriptor_name":"Nucleosides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo040215h","doi":"https://doi.org/10.1021/jo040215h","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo040215h","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":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":"pmid:15549827","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15549827","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1336839141","display_name":"HIGH RESOLUTION MASS SPECTROMETER","funder_award_id":"P41GM049631","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"id":"https://openalex.org/G2365099725","display_name":"ORGANOMETALLIC SYNTHESES OF BIOACTIVE COMPOUNDS","funder_award_id":"R01GM026178","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":42,"referenced_works":["https://openalex.org/W641636675","https://openalex.org/W1968170959","https://openalex.org/W1975803955","https://openalex.org/W1986001811","https://openalex.org/W1987026350","https://openalex.org/W1999909183","https://openalex.org/W2008542978","https://openalex.org/W2012867020","https://openalex.org/W2013086569","https://openalex.org/W2014938265","https://openalex.org/W2019193983","https://openalex.org/W2024287384","https://openalex.org/W2025914621","https://openalex.org/W2030538354","https://openalex.org/W2035744489","https://openalex.org/W2038701213","https://openalex.org/W2040141107","https://openalex.org/W2040935171","https://openalex.org/W2040985363","https://openalex.org/W2048041043","https://openalex.org/W2053584811","https://openalex.org/W2058189967","https://openalex.org/W2060404872","https://openalex.org/W2070619668","https://openalex.org/W2075868010","https://openalex.org/W2078548116","https://openalex.org/W2091974662","https://openalex.org/W2105925046","https://openalex.org/W2128068690","https://openalex.org/W2135104027","https://openalex.org/W2148625579","https://openalex.org/W2330735918","https://openalex.org/W2343881885","https://openalex.org/W2410387570","https://openalex.org/W2949606492","https://openalex.org/W2950930909","https://openalex.org/W2951781429","https://openalex.org/W2952634598","https://openalex.org/W2953257966","https://openalex.org/W2953328901","https://openalex.org/W4211254635","https://openalex.org/W4245431641"],"related_works":["https://openalex.org/W2952747705","https://openalex.org/W2953273744","https://openalex.org/W2111501004","https://openalex.org/W1989089460","https://openalex.org/W2952907478","https://openalex.org/W2994458442","https://openalex.org/W2585042754","https://openalex.org/W2060481714","https://openalex.org/W399347042","https://openalex.org/W2953257335"],"abstract_inverted_index":{"Carbocyclic":[0],"4'-methyl":[1],"and":[2,16,31,48],"4'-cyano":[3],"nucleoside":[4,23],"analogues":[5],"were":[6],"synthesized":[7],"using":[8],"the":[9,14,22,28,36,46],"Michael":[10],"reaction":[11],"to":[12,20],"introduce":[13,21],"4'-substituent":[15],"Pd-catalyzed":[17,37],"allylic":[18],"substitution":[19,38],"base.":[24],"Use":[25],"of":[26,45,51,56],"both":[27],"desired":[29],"beta-":[30],"undesired":[32],"alpha-1'-carbonate":[33],"diastereomers":[34],"in":[35,41],"was":[39],"demonstrated":[40],"principle":[42],"by":[43],"epimerization":[44],"alpha-diastereomer":[47],"kinetic":[49],"diastereodifferentiation":[50],"a":[52],"1:1":[53],"alpha/beta":[54],"mixture":[55],"1'-carbonates.":[57]},"counts_by_year":[{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":2}],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2019-06-27T00:00:00"}