{"id":"https://openalex.org/W2170733288","doi":"https://doi.org/10.1021/jo049724+","title":"Asymmetric Total Synthesis of (+)-Cannabisativine","display_name":"Asymmetric Total Synthesis of (+)-Cannabisativine","publication_year":2004,"publication_date":"2004-04-29","ids":{"openalex":"https://openalex.org/W2170733288","doi":"https://doi.org/10.1021/jo049724+","mag":"2170733288","pmid":"https://pubmed.ncbi.nlm.nih.gov/15287764"},"language":"en","primary_location":{"id":"doi:10.1021/jo049724+","doi":"https://doi.org/10.1021/jo049724+","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo049724+","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/A5014071118","display_name":"Jeffrey T. Kuethe","orcid":"https://orcid.org/0000-0001-8955-6010","observed_orcids":["https://orcid.org/0000-0001-8955-6010"]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jeffrey T. Kuethe","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5077943087","display_name":"Daniel L. Comins","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Daniel L. Comins","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I137902535"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.8176,"has_fulltext":false,"cited_by_count":56,"citation_normalized_percentile":{"value":0.90628977,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"69","issue":"16","first_page":"5219","last_page":"5231"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.79830002784729,"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":0.79830002784729,"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":0.05849999934434891,"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":0.05730000138282776,"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/asymmetric-total-synthesis","display_name":"asymmetric total synthesis","score":0.921999990940094},{"id":"https://openalex.org/keywords/natural-product-synthesis","display_name":"natural product synthesis","score":0.49300000071525574},{"id":"https://openalex.org/keywords/dihydropyridinones","display_name":"dihydropyridones","score":0.8199999928474426},{"id":"https://openalex.org/keywords/luche-reduction","display_name":"Luche reduction","score":0.9100000262260437},{"id":"https://openalex.org/keywords/diastereoselectivity","display_name":"diastereoselectivity","score":0.9269999861717224},{"id":"https://openalex.org/keywords/mukaiyama-michael-reaction","display_name":"Mukaiyama-Michael reaction","score":0.972000002861023},{"id":"https://openalex.org/keywords/tetrahydropyridines","display_name":"tetrahydropyridines","score":0.8970000147819519},{"id":"https://openalex.org/keywords/stereocontrol","display_name":"stereocontrol","score":0.47699999809265137}],"concepts":[{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.8223995566368103},{"id":"https://openalex.org/C2778874822","wikidata":"https://www.wikidata.org/wiki/Q368158","display_name":"Ketene","level":2,"score":0.8019832372665405},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7932555079460144},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.7304879426956177},{"id":"https://openalex.org/C2777731525","wikidata":"https://www.wikidata.org/wiki/Q421103","display_name":"Acetal","level":2,"score":0.6903417706489563},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.6758638620376587},{"id":"https://openalex.org/C2777221202","wikidata":"https://www.wikidata.org/wiki/Q2518436","display_name":"Pyridinium","level":2,"score":0.6709281802177429},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.6135777831077576},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.5927621126174927},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5602731108665466},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.5593751072883606},{"id":"https://openalex.org/C112423150","wikidata":"https://www.wikidata.org/wiki/Q642233","display_name":"Michael reaction","level":3,"score":0.526633083820343},{"id":"https://openalex.org/C25170562","wikidata":"https://www.wikidata.org/wiki/Q2052053","display_name":"Absolute configuration","level":2,"score":0.4947480857372284},{"id":"https://openalex.org/C2777738585","wikidata":"https://www.wikidata.org/wiki/Q170744","display_name":"Ketone","level":2,"score":0.491759330034256},{"id":"https://openalex.org/C5304478","wikidata":"https://www.wikidata.org/wiki/Q502457","display_name":"Silylation","level":3,"score":0.4775731861591339},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.26949846744537354},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.24279651045799255},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.15200603008270264},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"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":false},{"descriptor_ui":"D002186","descriptor_name":"Cannabinoids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D002186","descriptor_name":"Cannabinoids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009942","descriptor_name":"Organometallic Compounds","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011726","descriptor_name":"Pyridinium Compounds","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"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":"D019906","descriptor_name":"Nuclear Magnetic Resonance, Biomolecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo049724+","doi":"https://doi.org/10.1021/jo049724+","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo049724+","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:15287764","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15287764","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/G1902379259","display_name":"SYNTHESIS AND SYNTHETIC UTILITY OF 1-ACYLDIHYDROPYRIDINE","funder_award_id":"R01GM034442","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G6559500453","display_name":null,"funder_award_id":"GM34442","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"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":26,"referenced_works":["https://openalex.org/W69013672","https://openalex.org/W1566177353","https://openalex.org/W1966349181","https://openalex.org/W1968214465","https://openalex.org/W1971225732","https://openalex.org/W1980546476","https://openalex.org/W1980759435","https://openalex.org/W1996892864","https://openalex.org/W2008925748","https://openalex.org/W2010610278","https://openalex.org/W2019941613","https://openalex.org/W2037127130","https://openalex.org/W2052511948","https://openalex.org/W2054468412","https://openalex.org/W2059242926","https://openalex.org/W2073657491","https://openalex.org/W2076556331","https://openalex.org/W2094871139","https://openalex.org/W2107547396","https://openalex.org/W2321253207","https://openalex.org/W2323328967","https://openalex.org/W2951697664","https://openalex.org/W2952631744","https://openalex.org/W2952909701","https://openalex.org/W2953231904","https://openalex.org/W3005005514"],"related_works":["https://openalex.org/W1966349181","https://openalex.org/W2951054651","https://openalex.org/W2010610278","https://openalex.org/W2045451936","https://openalex.org/W1978724741","https://openalex.org/W2002351132","https://openalex.org/W2173865089","https://openalex.org/W2903856065","https://openalex.org/W3149734002","https://openalex.org/W2098830809"],"abstract_inverted_index":{"The":[0,17,75],"asymmetric":[1,128],"total":[2],"synthesis":[3,129],"of":[4,28,40,55,62,78,95,104,115,126,130,138],"natural":[5],"(+)-cannabisativine":[6],"1":[7],"was":[8,22],"completed":[9],"in":[10,30,68],"19":[11],"steps":[12,32],"and":[13,72,98],"7%":[14],"overall":[15],"yield.":[16],"key":[18],"synthetic":[19],"intermediate":[20],"29":[21],"prepared":[23],"with":[24,81,91,134],"a":[25,135],"high":[26,69,136],"degree":[27,137],"stereocontrol":[29],"12":[31,50],"starting":[33],"from":[34],"chiral":[35],"1-acylpyridinium":[36],"salt":[37,46],"10.":[38],"Addition":[39],"zinc":[41],"enolate":[42],"11":[43],"to":[44,110,123],"pyridinium":[45],"10":[47],"furnished":[48],"dihydropyridone":[49],"containing":[51],"two":[52],"contiguous":[53],"stereocenters":[54],"the":[56,101,111,116,124,131],"correct":[57],"absolute":[58],"configuration.":[59],"Luche":[60],"reduction":[61],"ketone":[63],"16":[64],"afforded":[65],"diol":[66],"17":[67],"yield":[70],"(96%)":[71],"excellent":[73],"diastereoselectivity.":[74],"Mukaiyama-Michael":[76],"reaction":[77],"pyridones":[79],"27a/b":[80],"O-silyl":[82],"ketene":[83],"acetal":[84],"32":[85],"gave":[86],"phenyl":[87],"selenyl":[88],"ketones":[89],"33a/b":[90],"complete":[92],"stereoselectivity.":[93],"Elimination":[94],"cis-beta-hydroxyselenides":[96],"34":[97],"35":[99],"effected":[100],"regiocontrolled":[102],"preparation":[103],"tetrahydropyridine":[105],"derivative":[106],"29.":[107],"Several":[108],"approaches":[109],"macrocyclic":[112],"ring":[113,118],"closure":[114],"13-membered":[117],"were":[119],"investigated,":[120],"ultimately":[121],"leading":[122],"completion":[125],"an":[127],"target":[132],"compound":[133],"stereocontrol.":[139]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":4},{"year":2014,"cited_by_count":3},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":2}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
