{"id":"https://openalex.org/W2014728070","doi":"https://doi.org/10.1021/jo702136b","title":"Stereoselective Total Syntheses of Three Lycopodium Alkaloids, (\u2212)-Magellanine, (+)-Magellaninone, and (+)-Paniculatine, Based on Two Pauson\u2212Khand Reactions","display_name":"Stereoselective Total Syntheses of Three Lycopodium Alkaloids, (\u2212)-Magellanine, (+)-Magellaninone, and (+)-Paniculatine, Based on Two Pauson\u2212Khand Reactions","publication_year":2007,"publication_date":"2007-11-29","ids":{"openalex":"https://openalex.org/W2014728070","doi":"https://doi.org/10.1021/jo702136b","mag":"2014728070","pmid":"https://pubmed.ncbi.nlm.nih.gov/18044932"},"language":"en","primary_location":{"id":"doi:10.1021/jo702136b","doi":"https://doi.org/10.1021/jo702136b","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo702136b","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/A5027626411","display_name":"Takashi Kozaka","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I10091056","display_name":"Kanazawa University","ror":"https://ror.org/02hwp6a56","country_code":"JP","type":"education","lineage":["https://openalex.org/I10091056"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Takashi Kozaka","raw_affiliation_strings":["Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan","institution_ids":["https://openalex.org/I10091056"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5014896119","display_name":"Naoki Miyakoshi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I10091056","display_name":"Kanazawa University","ror":"https://ror.org/02hwp6a56","country_code":"JP","type":"education","lineage":["https://openalex.org/I10091056"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Naoki Miyakoshi","raw_affiliation_strings":["Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan","institution_ids":["https://openalex.org/I10091056"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5057823553","display_name":"Chisato Mukai","orcid":"https://orcid.org/0000-0001-8621-1068","observed_orcids":["https://orcid.org/0000-0001-8621-1068"]},"institutions":[{"id":"https://openalex.org/I10091056","display_name":"Kanazawa University","ror":"https://ror.org/02hwp6a56","country_code":"JP","type":"education","lineage":["https://openalex.org/I10091056"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Chisato Mukai","raw_affiliation_strings":["Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan","institution_ids":["https://openalex.org/I10091056"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I10091056"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":5.039,"has_fulltext":false,"cited_by_count":84,"citation_normalized_percentile":{"value":0.96031421,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"72","issue":"26","first_page":"10147","last_page":"10154"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.9258000254631042,"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":0.9258000254631042,"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":0.04320000112056732,"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":0.010200000368058681,"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/lycopodium-alkaloids","display_name":"Lycopodium alkaloids","score":0.9160000085830688},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.8799999952316284},{"id":"https://openalex.org/keywords/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.9330000281333923},{"id":"https://openalex.org/keywords/pauson-khand-reaction","display_name":"Pauson-Khand reaction","score":0.9430000185966492},{"id":"https://openalex.org/keywords/intramolecular-pauson-khand-reaction","display_name":"intramolecular Pauson-Khand reaction","score":0.8529999852180481},{"id":"https://openalex.org/keywords/enynes","display_name":"enynes","score":0.8999999761581421}],"concepts":[{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.9412702918052673},{"id":"https://openalex.org/C2777376760","wikidata":"https://www.wikidata.org/wiki/Q903694","display_name":"Pauson\u2013Khand reaction","level":3,"score":0.9241304397583008},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.7432882785797119},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6943498253822327},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.6852445602416992},{"id":"https://openalex.org/C24961977","wikidata":"https://www.wikidata.org/wiki/Q225972","display_name":"Bicyclic molecule","level":2,"score":0.6272252202033997},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5921940803527832},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.464000403881073},{"id":"https://openalex.org/C2994471683","wikidata":"https://www.wikidata.org/wiki/Q899274","display_name":"Carbon skeleton","level":2,"score":0.4313523769378662},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.21200811862945557},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.05451035499572754}],"mesh":[{"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":false},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","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":"D032502","descriptor_name":"Lycopodium","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo702136b","doi":"https://doi.org/10.1021/jo702136b","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo702136b","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:18044932","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/18044932","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":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":35,"referenced_works":["https://openalex.org/W1968936262","https://openalex.org/W1972703201","https://openalex.org/W1980518130","https://openalex.org/W1984812746","https://openalex.org/W1985008400","https://openalex.org/W1985955208","https://openalex.org/W2005112216","https://openalex.org/W2010072635","https://openalex.org/W2010231362","https://openalex.org/W2010986404","https://openalex.org/W2023305066","https://openalex.org/W2033723013","https://openalex.org/W2063081431","https://openalex.org/W2074243775","https://openalex.org/W2089754723","https://openalex.org/W2092412515","https://openalex.org/W2096625672","https://openalex.org/W2097233091","https://openalex.org/W2103806108","https://openalex.org/W2114575672","https://openalex.org/W2128467610","https://openalex.org/W2178813757","https://openalex.org/W2179521914","https://openalex.org/W2414786766","https://openalex.org/W2949500099","https://openalex.org/W2949593910","https://openalex.org/W2949830831","https://openalex.org/W2950565521","https://openalex.org/W2950868701","https://openalex.org/W2951105867","https://openalex.org/W2952881857","https://openalex.org/W3004587346","https://openalex.org/W3005187241","https://openalex.org/W3005308991","https://openalex.org/W4233898158"],"related_works":["https://openalex.org/W2951523726","https://openalex.org/W1985955208","https://openalex.org/W2952031922","https://openalex.org/W2951907935","https://openalex.org/W2126593740","https://openalex.org/W7112094658","https://openalex.org/W2179521914","https://openalex.org/W4281769812","https://openalex.org/W2097233091","https://openalex.org/W3173336380"],"abstract_inverted_index":{"The":[0,21],"total":[1],"syntheses":[2,26],"of":[3,32,49,76],"(-)-magellanine,":[4],"(+)-magellaninone,":[5],"and":[6,46,73],"(+)-paniculatine":[7],"were":[8],"completed":[9],"from":[10],"diethyl":[11],"l-tartrate":[12],"via":[13],"the":[14,34,39,43,58,64,71,77],"common":[15],"intermediate":[16],"in":[17,24,52],"a":[18,53],"stereoselective":[19,55],"manner.":[20],"crucial":[22],"steps":[23],"these":[25,50],"involved":[27],"two":[28],"intramolecular":[29],"Pauson-Khand":[30,36,60],"reactions":[31],"enynes:":[33],"first":[35],"reaction":[37,61],"constructed":[38],"bicyclo[4.3.0]":[40],"carbon":[41],"framework,":[42],"corresponding":[44],"A":[45],"B":[47],"rings":[48,75],"alkaloids":[51],"highly":[54],"manner,":[56],"whereas":[57],"second":[59],"stereoselectively":[62],"produced":[63],"bicyclo[3.3.0]skeleton,":[65],"which":[66],"could":[67],"be":[68],"converted":[69],"into":[70],"C":[72],"D":[74],"target":[78],"natural":[79],"products.":[80]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":3},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":4},{"year":2020,"cited_by_count":4},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":6},{"year":2017,"cited_by_count":8},{"year":2016,"cited_by_count":4},{"year":2015,"cited_by_count":5},{"year":2014,"cited_by_count":3},{"year":2013,"cited_by_count":6},{"year":2012,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
