{"id":"https://openalex.org/W2324536749","doi":"https://doi.org/10.1021/jo202651t","title":"Asymmetric Total Synthesis of (+)-Virosine A via Sequential Nucleophilic Cyclizations onto an Activated Formamide","display_name":"Asymmetric Total Synthesis of (+)-Virosine A via Sequential Nucleophilic Cyclizations onto an Activated Formamide","publication_year":2012,"publication_date":"2012-03-05","ids":{"openalex":"https://openalex.org/W2324536749","doi":"https://doi.org/10.1021/jo202651t","mag":"2324536749","pmid":"https://pubmed.ncbi.nlm.nih.gov/22390172"},"language":"en","primary_location":{"id":"doi:10.1021/jo202651t","doi":"https://doi.org/10.1021/jo202651t","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo202651t","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","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://usherbrooke.scholaris.ca/bitstreams/e1276f9e-3521-43b0-87f5-4d84f815738a/download","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5007513649","display_name":"Guillaume B\u00e9langer","orcid":"https://orcid.org/0000-0002-7454-8760","observed_orcids":["https://orcid.org/0000-0002-7454-8760"]},"institutions":[{"id":"https://openalex.org/I135117807","display_name":"Universit\u00e9 de Sherbrooke","ror":"https://ror.org/00kybxq39","country_code":"CA","type":"education","lineage":["https://openalex.org/I135117807"]}],"countries":["CA"],"is_corresponding":true,"raw_author_name":"Guillaume B\u00e9langer","raw_affiliation_strings":["D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 boulevard Universit\u00e9,\rSherbrooke, Qu\u00e9bec J1K 2R1, Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 boulevard Universit\u00e9,\rSherbrooke, Qu\u00e9bec J1K 2R1, Canada","institution_ids":["https://openalex.org/I135117807"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5020432885","display_name":"Marianne Dupuis","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135117807","display_name":"Universit\u00e9 de Sherbrooke","ror":"https://ror.org/00kybxq39","country_code":"CA","type":"education","lineage":["https://openalex.org/I135117807"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"Marianne Dupuis","raw_affiliation_strings":["D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 boulevard Universit\u00e9,\rSherbrooke, Qu\u00e9bec J1K 2R1, Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 boulevard Universit\u00e9,\rSherbrooke, Qu\u00e9bec J1K 2R1, Canada","institution_ids":["https://openalex.org/I135117807"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5007621532","display_name":"Robin Larouche\u2010Gauthier","orcid":"https://orcid.org/0000-0003-1919-600X","observed_orcids":["https://orcid.org/0000-0003-1919-600X"]},"institutions":[{"id":"https://openalex.org/I135117807","display_name":"Universit\u00e9 de Sherbrooke","ror":"https://ror.org/00kybxq39","country_code":"CA","type":"education","lineage":["https://openalex.org/I135117807"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"Robin Larouche-Gauthier","raw_affiliation_strings":["D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 boulevard Universit\u00e9,\rSherbrooke, Qu\u00e9bec J1K 2R1, Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 boulevard Universit\u00e9,\rSherbrooke, Qu\u00e9bec J1K 2R1, Canada","institution_ids":["https://openalex.org/I135117807"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5007513649"],"corresponding_institution_ids":["https://openalex.org/I135117807"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.9138,"has_fulltext":true,"cited_by_count":36,"citation_normalized_percentile":{"value":0.83751243,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":91,"max":98},"biblio":{"volume":"77","issue":"7","first_page":"3215","last_page":"3221"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.98580002784729,"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":0.98580002784729,"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/T13971","display_name":"Isoquinoline Alkaloid Synthesis","score":0.006399999838322401,"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/T13124","display_name":"Chemical synthesis and alkaloids","score":0.0024999999441206455,"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/total-synthesis","display_name":"total synthesis","score":0.7590000033378601},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.9179999828338623},{"id":"https://openalex.org/keywords/tetracyclic-alkaloids","display_name":"tetracyclic alkaloids","score":0.8560000061988831},{"id":"https://openalex.org/keywords/nucleophilic-cyclization","display_name":"nucleophilic cyclization","score":0.9710000157356262},{"id":"https://openalex.org/keywords/mannich-reaction","display_name":"Mannich reaction","score":0.9210000038146973},{"id":"https://openalex.org/keywords/azabicyclo-2-2-2-octane","display_name":"azabicyclo[2.2.2]octane","score":0.9430000185966492}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9682438373565674},{"id":"https://openalex.org/C2776624427","wikidata":"https://www.wikidata.org/wiki/Q150681","display_name":"Octane","level":2,"score":0.7522602081298828},{"id":"https://openalex.org/C2778270854","wikidata":"https://www.wikidata.org/wiki/Q283917","display_name":"Formamide","level":2,"score":0.7017995119094849},{"id":"https://openalex.org/C2777667214","wikidata":"https://www.wikidata.org/wiki/Q70702","display_name":"Alkaloid","level":2,"score":0.7008312344551086},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.5914402604103088},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.5310870409011841},{"id":"https://openalex.org/C2780640045","wikidata":"https://www.wikidata.org/wiki/Q183055","display_name":"Mannich reaction","level":3,"score":0.5186535716056824},{"id":"https://openalex.org/C2781462491","wikidata":"https://www.wikidata.org/wiki/Q410234","display_name":"Piperidine","level":2,"score":0.5163625478744507},{"id":"https://openalex.org/C2778112365","wikidata":"https://www.wikidata.org/wiki/Q3511065","display_name":"Sequence (biology)","level":2,"score":0.5080904960632324},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5043824911117554},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3810776472091675},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000470","descriptor_name":"Alkaloids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000470","descriptor_name":"Alkaloids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D003500","descriptor_name":"Cyclization","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D005559","descriptor_name":"Formamides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006576","descriptor_name":"Heterocyclic Compounds, 4 or More Rings","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D006576","descriptor_name":"Heterocyclic Compounds, 4 or More Rings","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D019665","descriptor_name":"Euphorbiaceae","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":5,"locations":[{"id":"doi:10.1021/jo202651t","doi":"https://doi.org/10.1021/jo202651t","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo202651t","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:22390172","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/22390172","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:usherbrooke.scholaris.ca:11143/17298","doi":null,"is_oa":true,"landing_page_url":"http://hdl.handle.net/11143/17298","pdf_url":"https://usherbrooke.scholaris.ca/bitstreams/e1276f9e-3521-43b0-87f5-4d84f815738a/download","source":{"id":"https://openalex.org/S4306401321","display_name":"Knowledge UdeS (Institutional Deposit of the University of Sherbrooke)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I135117807","host_organization_name":"Universit\u00e9 de Sherbrooke","host_organization_lineage":["https://openalex.org/I135117807"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"Article"},{"id":"pmh:oai:savoirs.usherbrooke.ca:11143/17298","doi":null,"is_oa":true,"landing_page_url":"http://hdl.handle.net/11143/17298","pdf_url":null,"source":{"id":"https://openalex.org/S4306401321","display_name":"Knowledge UdeS (Institutional Deposit of the University of Sherbrooke)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I135117807","host_organization_name":"Universit\u00e9 de Sherbrooke","host_organization_lineage":["https://openalex.org/I135117807"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Article"},{"id":"mag:3151874513","doi":null,"is_oa":false,"landing_page_url":"http://agris.fao.org/agris-search/search.do?recordID=US201800039492","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":null,"is_accepted":false,"is_published":false,"raw_source_name":"The Journal of Organic Chemistry","raw_type":null}],"best_oa_location":{"id":"pmh:oai:usherbrooke.scholaris.ca:11143/17298","doi":null,"is_oa":true,"landing_page_url":"http://hdl.handle.net/11143/17298","pdf_url":"https://usherbrooke.scholaris.ca/bitstreams/e1276f9e-3521-43b0-87f5-4d84f815738a/download","source":{"id":"https://openalex.org/S4306401321","display_name":"Knowledge UdeS (Institutional Deposit of the University of Sherbrooke)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I135117807","host_organization_name":"Universit\u00e9 de Sherbrooke","host_organization_lineage":["https://openalex.org/I135117807"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"Article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320334593","display_name":"Natural Sciences and Engineering Research Council of Canada","ror":"https://ror.org/01h531d29"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W2324536749.pdf","grobid_xml":"https://content.openalex.org/works/W2324536749.grobid-xml"},"referenced_works_count":21,"referenced_works":["https://openalex.org/W1039637122","https://openalex.org/W1516793071","https://openalex.org/W1527942348","https://openalex.org/W1964454970","https://openalex.org/W1991700756","https://openalex.org/W2001922905","https://openalex.org/W2034322191","https://openalex.org/W2038256683","https://openalex.org/W2044206206","https://openalex.org/W2058760452","https://openalex.org/W2126158189","https://openalex.org/W2141705345","https://openalex.org/W2150955084","https://openalex.org/W2153698065","https://openalex.org/W2326513831","https://openalex.org/W2949326209","https://openalex.org/W2950263924","https://openalex.org/W2951348789","https://openalex.org/W2953150412","https://openalex.org/W4213271115","https://openalex.org/W4234148010"],"related_works":["https://openalex.org/W2030076063","https://openalex.org/W4388631311","https://openalex.org/W2773444154","https://openalex.org/W4234736062","https://openalex.org/W2027127570","https://openalex.org/W2953186184","https://openalex.org/W2929540862","https://openalex.org/W2150955084","https://openalex.org/W2620939292","https://openalex.org/W2038539775"],"abstract_inverted_index":{"The":[0,10,23],"first":[1],"synthesis":[2],"of":[3],"tetracyclic":[4],"alkaloid":[5,12],"virosine":[6],"A":[7],"is":[8],"reported.":[9],"natural":[11],"was":[13,26],"prepared":[14],"in":[15,19,38],"only":[16],"13":[17],"steps,":[18],"an":[20],"enantioenriched":[21],"form.":[22],"azabicyclo[2.2.2]octane":[24],"core":[25],"efficiently":[27],"assembled":[28],"using":[29],"a":[30],"key":[31],"Vilsmeier-Haack":[32],"and":[33],"Mannich":[34],"cyclizations":[35],"sequence":[36],"performed":[37],"one":[39],"pot.":[40]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2023,"cited_by_count":2},{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":5},{"year":2016,"cited_by_count":4},{"year":2015,"cited_by_count":3},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":4},{"year":2012,"cited_by_count":3}],"updated_date":"2026-11-07T11:25:07.637180","created_date":"2016-06-24T00:00:00"}
