{"id":"https://openalex.org/W2890976930","doi":"https://doi.org/10.1021/acs.orglett.8b02675","title":"Intramolecular Diels\u2013Alder Reaction of a Silyl-Substituted Vinylimidazole en Route to the Fully Substituted Cyclopentane Core of Oroidin Dimers","display_name":"Intramolecular Diels\u2013Alder Reaction of a Silyl-Substituted Vinylimidazole en Route to the Fully Substituted Cyclopentane Core of Oroidin Dimers","publication_year":2018,"publication_date":"2018-09-07","ids":{"openalex":"https://openalex.org/W2890976930","doi":"https://doi.org/10.1021/acs.orglett.8b02675","mag":"2890976930","pmid":"https://pubmed.ncbi.nlm.nih.gov/30192150"},"language":"en","primary_location":{"id":"doi:10.1021/acs.orglett.8b02675","doi":"https://doi.org/10.1021/acs.orglett.8b02675","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.8b02675","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","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/A5103159122","display_name":"Abhisek Ray","orcid":"https://orcid.org/0000-0002-0088-0576","observed_orcids":["https://orcid.org/0000-0002-0088-0576"]},"institutions":[{"id":"https://openalex.org/I189196454","display_name":"The University of Texas at Arlington","ror":"https://ror.org/019kgqr73","country_code":"US","type":"education","lineage":["https://openalex.org/I189196454"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Abhisek Ray","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States"],"raw_orcid":"https://orcid.org/0000-0002-0088-0576","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States","institution_ids":["https://openalex.org/I189196454"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5019971746","display_name":"Muhammed Yousufuddin","orcid":"https://orcid.org/0000-0002-4303-8303","observed_orcids":["https://orcid.org/0000-0002-4303-8303"]},"institutions":[{"id":"https://openalex.org/I189196454","display_name":"The University of Texas at Arlington","ror":"https://ror.org/019kgqr73","country_code":"US","type":"education","lineage":["https://openalex.org/I189196454"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Muhammed Yousufuddin","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States","institution_ids":["https://openalex.org/I189196454"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5031053900","display_name":"Delphine Gout","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I189196454","display_name":"The University of Texas at Arlington","ror":"https://ror.org/019kgqr73","country_code":"US","type":"education","lineage":["https://openalex.org/I189196454"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Delphine Gout","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States","institution_ids":["https://openalex.org/I189196454"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5074820584","display_name":"Carl J. Lovely","orcid":"https://orcid.org/0000-0001-7012-2001","observed_orcids":["https://orcid.org/0000-0001-7012-2001"]},"institutions":[{"id":"https://openalex.org/I189196454","display_name":"The University of Texas at Arlington","ror":"https://ror.org/019kgqr73","country_code":"US","type":"education","lineage":["https://openalex.org/I189196454"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Carl J. Lovely","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States"],"raw_orcid":"https://orcid.org/0000-0001-7012-2001","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Texas\u2014Arlington, Arlington, Texas 76019-0065, United States","institution_ids":["https://openalex.org/I189196454"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5074820584"],"corresponding_institution_ids":["https://openalex.org/I189196454"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.3942,"has_fulltext":false,"cited_by_count":16,"citation_normalized_percentile":{"value":0.4613978,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"20","issue":"18","first_page":"5964","last_page":"5968"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.5029000043869019,"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"}},"topics":[{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.5029000043869019,"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":0.18490000069141388,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.07750000059604645,"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/intramolecular-diels-alder-reaction","display_name":"intramolecular Diels-Alder reaction","score":0.9629999995231628},{"id":"https://openalex.org/keywords/vinylimidazole","display_name":"vinylimidazole","score":0.8560000061988831},{"id":"https://openalex.org/keywords/silyl-substituents","display_name":"silyl substituents","score":0.8579999804496765},{"id":"https://openalex.org/keywords/lactone-reduction","display_name":"lactone reduction","score":0.7480000257492065},{"id":"https://openalex.org/keywords/oxidative-rearrangement","display_name":"oxidative rearrangement","score":0.9639999866485596},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.5370000004768372}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9438931941986084},{"id":"https://openalex.org/C5304478","wikidata":"https://www.wikidata.org/wiki/Q502457","display_name":"Silylation","level":3,"score":0.8779422044754028},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.851088285446167},{"id":"https://openalex.org/C2778556512","wikidata":"https://www.wikidata.org/wiki/Q80260","display_name":"Cyclopentane","level":2,"score":0.8202062845230103},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.6958432793617249},{"id":"https://openalex.org/C2779940776","wikidata":"https://www.wikidata.org/wiki/Q375669","display_name":"Diels\u2013Alder reaction","level":3,"score":0.5982170701026917},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.45608067512512207},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4482722580432892},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3760398030281067},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.33171546459198},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.2742409110069275}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/acs.orglett.8b02675","doi":"https://doi.org/10.1021/acs.orglett.8b02675","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.8b02675","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:30192150","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/30192150","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":"Organic letters","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G6821664128","display_name":null,"funder_award_id":"Y-1362","funder_id":"https://openalex.org/F4320306196","funder_display_name":"Welch Foundation"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"},{"id":"https://openalex.org/F4320306196","display_name":"Welch Foundation","ror":"https://ror.org/00np6vq88"},{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":62,"referenced_works":["https://openalex.org/W1885480841","https://openalex.org/W1964288239","https://openalex.org/W1965679115","https://openalex.org/W1972950963","https://openalex.org/W1976422565","https://openalex.org/W1981308166","https://openalex.org/W1982659314","https://openalex.org/W1986795310","https://openalex.org/W1995706277","https://openalex.org/W1997085899","https://openalex.org/W2002804752","https://openalex.org/W2005388938","https://openalex.org/W2013953759","https://openalex.org/W2017986224","https://openalex.org/W2021218835","https://openalex.org/W2026566870","https://openalex.org/W2028093561","https://openalex.org/W2032722938","https://openalex.org/W2036823284","https://openalex.org/W2038739450","https://openalex.org/W2041184972","https://openalex.org/W2042058937","https://openalex.org/W2043759162","https://openalex.org/W2053768039","https://openalex.org/W2063431599","https://openalex.org/W2065169307","https://openalex.org/W2067211398","https://openalex.org/W2069317185","https://openalex.org/W2071402725","https://openalex.org/W2079782011","https://openalex.org/W2081660555","https://openalex.org/W2083560204","https://openalex.org/W2085820059","https://openalex.org/W2090789863","https://openalex.org/W2094404562","https://openalex.org/W2106882567","https://openalex.org/W2122153163","https://openalex.org/W2135007451","https://openalex.org/W2140905597","https://openalex.org/W2143518338","https://openalex.org/W2144301888","https://openalex.org/W2149606582","https://openalex.org/W2161998264","https://openalex.org/W2165408169","https://openalex.org/W2174022107","https://openalex.org/W2174997454","https://openalex.org/W2272054561","https://openalex.org/W2296195271","https://openalex.org/W2321822226","https://openalex.org/W2322518934","https://openalex.org/W2325587049","https://openalex.org/W2564935928","https://openalex.org/W2572172611","https://openalex.org/W2593840567","https://openalex.org/W2797657890","https://openalex.org/W2799830120","https://openalex.org/W2807927635","https://openalex.org/W2950732851","https://openalex.org/W2952280063","https://openalex.org/W2952606391","https://openalex.org/W3008009061","https://openalex.org/W3171062853"],"related_works":["https://openalex.org/W2013953759","https://openalex.org/W1981308166","https://openalex.org/W4412816553","https://openalex.org/W2051468859","https://openalex.org/W2053768039","https://openalex.org/W2118083007","https://openalex.org/W2013208905","https://openalex.org/W2080102243","https://openalex.org/W2116109877","https://openalex.org/W1991017654"],"abstract_inverted_index":{"An":[0],"intramolecular":[1],"Diels-Alder":[2],"reaction":[3],"of":[4,12,21,41],"a":[5,9,27,35],"silyl-substituted":[6],"vinylimidazole":[7],"delivers":[8],"diastereomeric":[10],"mixture":[11],"C4-silyl":[13],"functionalized":[14],"dihydrobenzimidazoles.":[15],"Subsequent":[16],"diastereoselective":[17],"reduction":[18],"and":[19,54],"elaboration":[20],"the":[22,42,49],"lactone":[23],"gives":[24],"rise":[25],"to":[26,48],"polysubstituted":[28],"tetrahydrobenzimidazole,":[29],"which,":[30],"upon":[31],"oxidative":[32],"rearrangement,":[33],"affords":[34],"single":[36],"spirofused":[37],"imidazolone":[38],"containing":[39],"all":[40],"relevant":[43],"functionality":[44],"for":[45],"an":[46],"approach":[47],"oroidin":[50],"dimers":[51],"axinellamine,":[52],"massadine,":[53],"palau'amine.":[55]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":7},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":3}],"updated_date":"2026-08-21T09:56:20.448147","created_date":"2018-09-27T00:00:00"}