{"id":"https://openalex.org/W2154863797","doi":"https://doi.org/10.1021/ja4023557","title":"Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B","display_name":"Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B","publication_year":2013,"publication_date":"2013-03-29","ids":{"openalex":"https://openalex.org/W2154863797","doi":"https://doi.org/10.1021/ja4023557","mag":"2154863797","pmid":"https://pubmed.ncbi.nlm.nih.gov/23540731","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/3662218"},"language":"en","primary_location":{"id":"doi:10.1021/ja4023557","doi":"https://doi.org/10.1021/ja4023557","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja4023557","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","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://www.ncbi.nlm.nih.gov/pmc/articles/3662218","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5058330488","display_name":"Madeleine E. Kieffer","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Madeleine E. Kieffer","raw_affiliation_strings":["The Warren and Katharine Schlinger Laboratory for Chemistry\rand Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California\r91125, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"The Warren and Katharine Schlinger Laboratory for Chemistry\rand Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California\r91125, United States","institution_ids":["https://openalex.org/I122411786"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5083379859","display_name":"Kangway V. Chuang","orcid":"https://orcid.org/0000-0002-0652-8071","observed_orcids":["https://orcid.org/0000-0002-0652-8071"]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kangway V. Chuang","raw_affiliation_strings":["The Warren and Katharine Schlinger Laboratory for Chemistry\rand Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California\r91125, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"The Warren and Katharine Schlinger Laboratory for Chemistry\rand Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California\r91125, United States","institution_ids":["https://openalex.org/I122411786"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5038661637","display_name":"Sarah E. Reisman","orcid":"https://orcid.org/0000-0001-8244-9300","observed_orcids":["https://orcid.org/0000-0001-8244-9300"]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Sarah E. Reisman","raw_affiliation_strings":["The Warren and Katharine Schlinger Laboratory for Chemistry\rand Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California\r91125, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"The Warren and Katharine Schlinger Laboratory for Chemistry\rand Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California\r91125, United States","institution_ids":["https://openalex.org/I122411786"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5038661637"],"corresponding_institution_ids":["https://openalex.org/I122411786"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":9.5895,"has_fulltext":false,"cited_by_count":151,"citation_normalized_percentile":{"value":0.989792,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":96,"max":100},"biblio":{"volume":"135","issue":"15","first_page":"5557","last_page":"5560"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.4894999861717224,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.4894999861717224,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.22130000591278076,"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":0.039500001817941666,"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/copper-catalysis","display_name":"copper catalysis","score":0.9240000247955322},{"id":"https://openalex.org/keywords/tryptophan-derivatives","display_name":"tryptophan derivatives","score":0.9990000128746033},{"id":"https://openalex.org/keywords/pyrroloindolines","display_name":"pyrroloindolines","score":0.8339999914169312},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.972000002861023},{"id":"https://openalex.org/keywords/natural-product-synthesis","display_name":"natural product synthesis","score":0.6890000104904175}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9864281415939331},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.800233006477356},{"id":"https://openalex.org/C2776706248","wikidata":"https://www.wikidata.org/wiki/Q181003","display_name":"Tryptophan","level":3,"score":0.7342531681060791},{"id":"https://openalex.org/C544778455","wikidata":"https://www.wikidata.org/wiki/Q753","display_name":"Copper","level":2,"score":0.7108925580978394},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.6540670394897461},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6061232686042786},{"id":"https://openalex.org/C204241405","wikidata":"https://www.wikidata.org/wiki/Q461499","display_name":"Transformation (genetics)","level":3,"score":0.5299478769302368},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4603360593318939},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.1110914945602417},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.06052285432815552},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","level":2,"score":0.0},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003300","descriptor_name":"Copper","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":"D014364","descriptor_name":"Tryptophan","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D054659","descriptor_name":"Diketopiperazines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D054659","descriptor_name":"Diketopiperazines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":5,"locations":[{"id":"doi:10.1021/ja4023557","doi":"https://doi.org/10.1021/ja4023557","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja4023557","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:23540731","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/23540731","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":"Journal of the American Chemical Society","raw_type":"Journal Article"},{"id":"pmh:oai:europepmc.org:2967354","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3662218","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:3662218","doi":null,"is_oa":true,"landing_page_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC3662218/","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"J Am Chem Soc","raw_type":"Text"},{"id":"pmh:oai:authors.library.caltech.edu:38761","doi":null,"is_oa":false,"landing_page_url":"https://resolver.caltech.edu/CaltechAUTHORS:20130603-133349209","pdf_url":null,"source":{"id":"https://openalex.org/S4306402161","display_name":"CaltechAUTHORS (California Institute of Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I122411786","host_organization_name":"California Institute of Technology","host_organization_lineage":["https://openalex.org/I122411786"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Article"}],"best_oa_location":{"id":"pmh:oai:europepmc.org:2967354","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3662218","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G7386764685","display_name":null,"funder_award_id":"RGM097582A","funder_id":"https://openalex.org/F4320332505","funder_display_name":"U.S. Public Health Service"},{"id":"https://openalex.org/G7565359147","display_name":"New Methods and Strategies for the Synthesis of ETP Natural Products","funder_award_id":"R01GM097582","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320332505","display_name":"U.S. Public Health Service","ror":"https://ror.org/05xf94514"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":54,"referenced_works":["https://openalex.org/W117906604","https://openalex.org/W1594718675","https://openalex.org/W1972836172","https://openalex.org/W1976973071","https://openalex.org/W1979844089","https://openalex.org/W1980797373","https://openalex.org/W1982217207","https://openalex.org/W1984220526","https://openalex.org/W1985669737","https://openalex.org/W1994889937","https://openalex.org/W1996939845","https://openalex.org/W2001145375","https://openalex.org/W2001404702","https://openalex.org/W2001614462","https://openalex.org/W2002178004","https://openalex.org/W2008750869","https://openalex.org/W2012042628","https://openalex.org/W2018988563","https://openalex.org/W2020615894","https://openalex.org/W2027057367","https://openalex.org/W2031952024","https://openalex.org/W2032003868","https://openalex.org/W2044941886","https://openalex.org/W2048272419","https://openalex.org/W2048651897","https://openalex.org/W2049070043","https://openalex.org/W2071053863","https://openalex.org/W2078030302","https://openalex.org/W2079835265","https://openalex.org/W2083799994","https://openalex.org/W2088917554","https://openalex.org/W2089459394","https://openalex.org/W2090748242","https://openalex.org/W2111589261","https://openalex.org/W2117051429","https://openalex.org/W2123624477","https://openalex.org/W2128704237","https://openalex.org/W2135467311","https://openalex.org/W2137853525","https://openalex.org/W2138076197","https://openalex.org/W2146373532","https://openalex.org/W2149642996","https://openalex.org/W2162637930","https://openalex.org/W2168300222","https://openalex.org/W2168502620","https://openalex.org/W2171852765","https://openalex.org/W2173038487","https://openalex.org/W2344486398","https://openalex.org/W2937211748","https://openalex.org/W2950104649","https://openalex.org/W2950497827","https://openalex.org/W2953341102","https://openalex.org/W3182029638","https://openalex.org/W4300550492"],"related_works":["https://openalex.org/W1121977940","https://openalex.org/W2952416785","https://openalex.org/W3037512872","https://openalex.org/W2137853525","https://openalex.org/W4232363767","https://openalex.org/W2002954178","https://openalex.org/W2744229323","https://openalex.org/W2766155821","https://openalex.org/W2079723724","https://openalex.org/W1544273508"],"abstract_inverted_index":{"A":[0,44],"copper-catalyzed":[1],"arylation":[2],"of":[3,30,39],"tryptophan":[4],"derivatives":[5],"is":[6,33],"reported.":[7],"The":[8,28],"reaction":[9],"proceeds":[10],"with":[11],"high":[12],"site-":[13],"and":[14,45],"diastereoselectivity":[15],"to":[16],"provide":[17],"aryl":[18],"pyrroloindoline":[19],"products":[20,42],"in":[21,35],"one":[22],"step":[23],"from":[24],"simple":[25],"starting":[26],"materials.":[27],"utility":[29],"this":[31],"transformation":[32],"highlighted":[34],"the":[36,40],"five-step":[37],"syntheses":[38],"natural":[41],"(+)-naseseazine":[43],"B.":[46]},"counts_by_year":[{"year":2026,"cited_by_count":6},{"year":2025,"cited_by_count":8},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":8},{"year":2021,"cited_by_count":11},{"year":2020,"cited_by_count":8},{"year":2019,"cited_by_count":8},{"year":2018,"cited_by_count":11},{"year":2017,"cited_by_count":13},{"year":2016,"cited_by_count":13},{"year":2015,"cited_by_count":23},{"year":2014,"cited_by_count":20},{"year":2013,"cited_by_count":13}],"updated_date":"2026-11-10T11:39:43.021295","created_date":"2016-06-24T00:00:00"}