{"id":"https://openalex.org/W2001077641","doi":"https://doi.org/10.1021/ol061334h","title":"Six-Step Synthesis of (S)-Brevicolline from (S)-Nicotine","display_name":"Six-Step Synthesis of (S)-Brevicolline from (S)-Nicotine","publication_year":2006,"publication_date":"2006-07-13","ids":{"openalex":"https://openalex.org/W2001077641","doi":"https://doi.org/10.1021/ol061334h","mag":"2001077641","pmid":"https://pubmed.ncbi.nlm.nih.gov/16869657"},"language":"en","primary_location":{"id":"doi:10.1021/ol061334h","doi":"https://doi.org/10.1021/ol061334h","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol061334h","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/A5049183478","display_name":"Florence F. Wagner","orcid":"https://orcid.org/0000-0001-8981-0330","observed_orcids":["https://orcid.org/0000-0001-8981-0330"]},"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":"Florence F. Wagner","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA"],"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"]},{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA","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":1.4942,"has_fulltext":false,"cited_by_count":32,"citation_normalized_percentile":{"value":0.79044054,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"8","issue":"16","first_page":"3549","last_page":"3552"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13188","display_name":"Synthesis and bioactivity of alkaloids","score":0.7846999764442444,"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/T13188","display_name":"Synthesis and bioactivity of alkaloids","score":0.7846999764442444,"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/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.2037000060081482,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.002199999988079071,"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/nicotine","display_name":"nicotine","score":0.9210000038146973},{"id":"https://openalex.org/keywords/beta-carbolines","display_name":"\u03b2-carbolines","score":0.9649999737739563},{"id":"https://openalex.org/keywords/enantiopure-synthesis","display_name":"enantiopure synthesis","score":0.6959999799728394},{"id":"https://openalex.org/keywords/suzuki-miyaura-coupling","display_name":"Suzuki coupling","score":0.9639999866485596},{"id":"https://openalex.org/keywords/regioselective-substitution","display_name":"regioselective substitution","score":0.6850000023841858},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.5389999747276306}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.921529233455658},{"id":"https://openalex.org/C93237805","wikidata":"https://www.wikidata.org/wiki/Q5375227","display_name":"Enantiopure drug","level":4,"score":0.916817307472229},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.7613796591758728},{"id":"https://openalex.org/C2779547902","wikidata":"https://www.wikidata.org/wiki/Q28086552","display_name":"Nicotine","level":2,"score":0.7344034910202026},{"id":"https://openalex.org/C198503264","wikidata":"https://www.wikidata.org/wiki/Q471635","display_name":"Amination","level":3,"score":0.731273353099823},{"id":"https://openalex.org/C2777667214","wikidata":"https://www.wikidata.org/wiki/Q70702","display_name":"Alkaloid","level":2,"score":0.6869878768920898},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.6471588611602783},{"id":"https://openalex.org/C2779485729","wikidata":"https://www.wikidata.org/wiki/Q210385","display_name":"Pyridine","level":2,"score":0.6034889817237854},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5021343231201172},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3901408910751343},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.26566648483276367},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.24216362833976746},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.13849878311157227},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.061371058225631714},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.0},{"id":"https://openalex.org/C169760540","wikidata":"https://www.wikidata.org/wiki/Q207011","display_name":"Neuroscience","level":1,"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":"Q000302","qualifier_name":"isolation & purification","is_major_topic":false},{"descriptor_ui":"D000470","descriptor_name":"Alkaloids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002243","descriptor_name":"Carbolines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D002243","descriptor_name":"Carbolines","qualifier_ui":"Q000302","qualifier_name":"isolation & purification","is_major_topic":false},{"descriptor_ui":"D002243","descriptor_name":"Carbolines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D007211","descriptor_name":"Indoles","qualifier_ui":"Q000302","qualifier_name":"isolation & purification","is_major_topic":false},{"descriptor_ui":"D007211","descriptor_name":"Indoles","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009538","descriptor_name":"Nicotine","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":"D031255","descriptor_name":"Carex Plant","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ol061334h","doi":"https://doi.org/10.1021/ol061334h","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol061334h","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:16869657","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16869657","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":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":18,"referenced_works":["https://openalex.org/W1966870647","https://openalex.org/W1980869830","https://openalex.org/W1982555225","https://openalex.org/W1984921272","https://openalex.org/W1990187247","https://openalex.org/W1995391435","https://openalex.org/W2006288703","https://openalex.org/W2018063680","https://openalex.org/W2060313556","https://openalex.org/W2064237032","https://openalex.org/W2077224764","https://openalex.org/W2077955137","https://openalex.org/W2078206080","https://openalex.org/W2949147327","https://openalex.org/W2949532792","https://openalex.org/W2950835969","https://openalex.org/W2951259064","https://openalex.org/W2951510481"],"related_works":["https://openalex.org/W2027575129","https://openalex.org/W1975478662","https://openalex.org/W2021828450","https://openalex.org/W4300796100","https://openalex.org/W4410523580","https://openalex.org/W2523653735","https://openalex.org/W2060515941","https://openalex.org/W2043277738","https://openalex.org/W2151638287","https://openalex.org/W2951609240"],"abstract_inverted_index":{"[reaction:":[0],"see":[1],"text]":[2],"A":[3],"six-step":[4],"synthesis":[5],"of":[6,14,18],"(S)-brevicolline":[7],"from":[8],"(S)-nicotine":[9],"is":[10],"reported.":[11],"Regioselective":[12],"trisubstitution":[13],"the":[15,30],"pyridine":[16],"ring":[17],"nicotine,":[19],"followed":[20],"by":[21],"successive":[22],"Suzuki":[23],"cross-coupling":[24],"and":[25],"Buchwald":[26],"amination":[27],"reactions,":[28],"afforded":[29],"enantiopure":[31],"beta-carboline":[32],"alkaloid,":[33],"brevicolline.":[34]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":3},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2016,"cited_by_count":2},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}