{"id":"https://openalex.org/W3138034132","doi":"https://doi.org/10.1002/anie.202102518","title":"Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**","display_name":"Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**","publication_year":2021,"publication_date":"2021-03-26","ids":{"openalex":"https://openalex.org/W3138034132","doi":"https://doi.org/10.1002/anie.202102518","mag":"3138034132","pmid":"https://pubmed.ncbi.nlm.nih.gov/33769684","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/8252720"},"language":"en","primary_location":{"id":"doi:10.1002/anie.202102518","doi":"https://doi.org/10.1002/anie.202102518","is_oa":true,"landing_page_url":"https://doi.org/10.1002/anie.202102518","pdf_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202102518","source":{"id":"https://openalex.org/S67393510","display_name":"Angewandte Chemie International Edition","issn_l":"1433-7851","issn":["1433-7851","1521-3773"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie International Edition","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","datacite","pubmed"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202102518","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5102107530","display_name":"Guoli He","orcid":"https://orcid.org/0000-0002-0620-0519","observed_orcids":["https://orcid.org/0000-0002-0620-0519"]},"institutions":[{"id":"https://openalex.org/I75951250","display_name":"Freie Universit\u00e4t Berlin","ror":"https://ror.org/046ak2485","country_code":"DE","type":"education","lineage":["https://openalex.org/I75951250"]}],"countries":["DE"],"is_corresponding":false,"raw_author_name":"Guoli He","raw_affiliation_strings":["Freie Universit\u00e4t Berlin Institute of Chemistry and Biochemistry Takustrasse 3 14195 Berlin Germany"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Freie Universit\u00e4t Berlin Institute of Chemistry and Biochemistry Takustrasse 3 14195 Berlin Germany","institution_ids":["https://openalex.org/I75951250"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5040055598","display_name":"Benjamin List","orcid":"https://orcid.org/0000-0002-9804-599X","observed_orcids":["https://orcid.org/0000-0002-9804-599X"]},"institutions":[{"id":"https://openalex.org/I4210090782","display_name":"Max-Planck-Institut f\u00fcr Kohlenforschung","ror":"https://ror.org/00a7vgh58","country_code":"DE","type":"facility","lineage":["https://openalex.org/I149899117","https://openalex.org/I4210090782"]}],"countries":["DE"],"is_corresponding":true,"raw_author_name":"Benjamin List","raw_affiliation_strings":["Max-Planck-Institut f\u00fcr Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 M\u00fclheim an der Ruhr Germany"],"raw_orcid":"https://orcid.org/0000-0002-9804-599X","affiliations":[{"raw_affiliation_string":"Max-Planck-Institut f\u00fcr Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 M\u00fclheim an der Ruhr Germany","institution_ids":["https://openalex.org/I4210090782"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5039921470","display_name":"Mathias Christmann","orcid":"https://orcid.org/0000-0001-9313-2392","observed_orcids":["https://orcid.org/0000-0001-9313-2392"]},"institutions":[{"id":"https://openalex.org/I75951250","display_name":"Freie Universit\u00e4t Berlin","ror":"https://ror.org/046ak2485","country_code":"DE","type":"education","lineage":["https://openalex.org/I75951250"]}],"countries":["DE"],"is_corresponding":true,"raw_author_name":"Mathias Christmann","raw_affiliation_strings":["Freie Universit\u00e4t Berlin Institute of Chemistry and Biochemistry Takustrasse 3 14195 Berlin Germany"],"raw_orcid":"https://orcid.org/0000-0001-9313-2392","affiliations":[{"raw_affiliation_string":"Freie Universit\u00e4t Berlin Institute of Chemistry and Biochemistry Takustrasse 3 14195 Berlin Germany","institution_ids":["https://openalex.org/I75951250"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5039921470","https://openalex.org/A5040055598"],"corresponding_institution_ids":["https://openalex.org/I4210090782","https://openalex.org/I75951250"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":{"value":5000,"currency":"USD","value_usd":5000},"fwci":2.3524,"has_fulltext":true,"cited_by_count":49,"citation_normalized_percentile":{"value":0.90765543,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":96,"max":99},"biblio":{"volume":"60","issue":"24","first_page":"13591","last_page":"13596"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13188","display_name":"Synthesis and bioactivity of alkaloids","score":0.8154000043869019,"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":0.8154000043869019,"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":0.13130000233650208,"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":0.029500000178813934,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"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"}}],"keywords":[{"id":"https://openalex.org/keywords/polycyclic-alkaloids","display_name":"polycyclic alkaloids","score":0.9850000143051147},{"id":"https://openalex.org/keywords/carbonyl-activation","display_name":"carbonyl activation","score":0.8889999985694885},{"id":"https://openalex.org/keywords/hirsutine","display_name":"hirsutine","score":0.7839999794960022},{"id":"https://openalex.org/keywords/rhynchophylline","display_name":"rhynchophylline","score":0.9929999709129333},{"id":"https://openalex.org/keywords/isorhynchophylline","display_name":"isorhynchophylline","score":0.9990000128746033},{"id":"https://openalex.org/keywords/beta-carbolines","display_name":"\u03b2-carbolines","score":0.9509999752044678},{"id":"https://openalex.org/keywords/oxindole-alkaloids","display_name":"oxindole alkaloids","score":0.9599999785423279},{"id":"https://openalex.org/keywords/berberine-alkaloids","display_name":"berberine alkaloids","score":0.8629999756813049},{"id":"https://openalex.org/keywords/asymmetric-cyclization","display_name":"asymmetric cyclization","score":0.8149999976158142},{"id":"https://openalex.org/keywords/protecting-group-free-synthesis","display_name":"protecting group-free synthesis","score":0.8790000081062317},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.6980000138282776}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5777996778488159},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3982114791870117},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.36967790126800537}],"mesh":[],"locations_count":7,"locations":[{"id":"doi:10.1002/anie.202102518","doi":"https://doi.org/10.1002/anie.202102518","is_oa":true,"landing_page_url":"https://doi.org/10.1002/anie.202102518","pdf_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202102518","source":{"id":"https://openalex.org/S67393510","display_name":"Angewandte Chemie International Edition","issn_l":"1433-7851","issn":["1433-7851","1521-3773"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie International Edition","raw_type":"journal-article"},{"id":"doi:10.26434/chemrxiv.14054558.v1","doi":"https://doi.org/10.26434/chemrxiv.14054558.v1","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.14054558.v1","pdf_url":null,"source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},{"id":"pmh:oai:pubmedcentral.nih.gov:8252720","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/8252720","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":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angew Chem Int Ed Engl","raw_type":"Text"},{"id":"pmid:33769684","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/33769684","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":"Angewandte Chemie (International ed. in English)","raw_type":"Journal Article"},{"id":"pmh:oai:figshare.com:article/14054558","doi":null,"is_oa":true,"landing_page_url":"https://figshare.com/articles/preprint/Unified_Synthesis_of_Polycyclic_Alkaloids_via_Complementary_Carbonyl_Activation/14054558","pdf_url":null,"source":{"id":"https://openalex.org/S4377196282","display_name":"Figshare","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4210132348","host_organization_name":"Figshare (United Kingdom)","host_organization_lineage":["https://openalex.org/I4210132348"],"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":"Text"},{"id":"pmh:oai:refubium.fu-berlin.de:fub188/30939","doi":null,"is_oa":true,"landing_page_url":"https://refubium.fu-berlin.de/handle/fub188/30939","pdf_url":null,"source":{"id":"https://openalex.org/S4306402444","display_name":"Refubium (Universit\u00e4tsbibliothek der Freien Universit\u00e4t Berlin)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I75951250","host_organization_name":"Freie Universit\u00e4t Berlin","host_organization_lineage":["https://openalex.org/I75951250"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"doc-type:article"},{"id":"doi:10.17169/refubium-30678","doi":"https://doi.org/10.17169/refubium-30678","is_oa":true,"landing_page_url":"https://doi.org/10.17169/refubium-30678","pdf_url":null,"source":{"id":"https://openalex.org/S7407052913","display_name":"Universit\u00e4tsbibliothek der FU Berlin Hochschulschriftenstelle u. Dokumentenserver","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":null,"is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"article-journal"}],"best_oa_location":{"id":"doi:10.1002/anie.202102518","doi":"https://doi.org/10.1002/anie.202102518","is_oa":true,"landing_page_url":"https://doi.org/10.1002/anie.202102518","pdf_url":"https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/anie.202102518","source":{"id":"https://openalex.org/S67393510","display_name":"Angewandte Chemie International Edition","issn_l":"1433-7851","issn":["1433-7851","1521-3773"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie International Edition","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320322725","display_name":"China Scholarship Council","ror":"https://ror.org/04atp4p48"},{"id":"https://openalex.org/F4320324521","display_name":"Freie Universit\u00e4t Berlin","ror":null}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W3138034132.pdf","grobid_xml":"https://content.openalex.org/works/W3138034132.grobid-xml"},"referenced_works_count":78,"referenced_works":["https://openalex.org/W1766684730","https://openalex.org/W1947062381","https://openalex.org/W1968635147","https://openalex.org/W1969641609","https://openalex.org/W1976163678","https://openalex.org/W1983329707","https://openalex.org/W1984700034","https://openalex.org/W1992661021","https://openalex.org/W1996068510","https://openalex.org/W1996608836","https://openalex.org/W1998740595","https://openalex.org/W1998873537","https://openalex.org/W2004081456","https://openalex.org/W2004607992","https://openalex.org/W2008224435","https://openalex.org/W2014095591","https://openalex.org/W2023014220","https://openalex.org/W2039861262","https://openalex.org/W2040044175","https://openalex.org/W2041513075","https://openalex.org/W2054551672","https://openalex.org/W2057846163","https://openalex.org/W2059869007","https://openalex.org/W2070145804","https://openalex.org/W2091868395","https://openalex.org/W2093564759","https://openalex.org/W2103808099","https://openalex.org/W2109136745","https://openalex.org/W2113573800","https://openalex.org/W2113600008","https://openalex.org/W2114741594","https://openalex.org/W2125756198","https://openalex.org/W2126421959","https://openalex.org/W2127311179","https://openalex.org/W2128708905","https://openalex.org/W2133212125","https://openalex.org/W2146885184","https://openalex.org/W2149831012","https://openalex.org/W2153721661","https://openalex.org/W2154842755","https://openalex.org/W2156850248","https://openalex.org/W2167137322","https://openalex.org/W2167377787","https://openalex.org/W2236616254","https://openalex.org/W2249405578","https://openalex.org/W2263023729","https://openalex.org/W2282408694","https://openalex.org/W2295583169","https://openalex.org/W2323222556","https://openalex.org/W2326314717","https://openalex.org/W2327850356","https://openalex.org/W2330408076","https://openalex.org/W2395593463","https://openalex.org/W2396073199","https://openalex.org/W2406527150","https://openalex.org/W2406617505","https://openalex.org/W2513317295","https://openalex.org/W2514435757","https://openalex.org/W2545338874","https://openalex.org/W2549337903","https://openalex.org/W2549852156","https://openalex.org/W2582342142","https://openalex.org/W2588876601","https://openalex.org/W2762797177","https://openalex.org/W2769506353","https://openalex.org/W2792157466","https://openalex.org/W2889304413","https://openalex.org/W2903781986","https://openalex.org/W2947030310","https://openalex.org/W2951339491","https://openalex.org/W2958829488","https://openalex.org/W3011366455","https://openalex.org/W3012086472","https://openalex.org/W3049477895","https://openalex.org/W3205887727","https://openalex.org/W4235073603","https://openalex.org/W4235118678","https://openalex.org/W4237482149"],"related_works":["https://openalex.org/W4244550490","https://openalex.org/W4399046078","https://openalex.org/W1982415015","https://openalex.org/W2335385225","https://openalex.org/W3037661601","https://openalex.org/W7097057799","https://openalex.org/W2071553185","https://openalex.org/W7221773025","https://openalex.org/W4416186893","https://openalex.org/W4385230818"],"abstract_inverted_index":{"A":[0],"complementary":[1],"dual":[2],"carbonyl":[3],"activation":[4],"strategy":[5],"for":[6],"the":[7,18],"synthesis":[8,19,38,68],"of":[9,20,51,69],"polycyclic":[10],"alkaloids":[11,22,58],"has":[12],"been":[13,63],"developed.":[14],"Successful":[15],"applications":[16],"include":[17],"tetracyclic":[21],"harmalanine":[23],"and":[24,30,43,56,60],"harmalacinine,":[25],"pentacyclic":[26],"indoloquinolizidine":[27],"alkaloid":[28,33,71],"nortetoyobyrine,":[29],"octacyclic":[31],"\u03b2-carboline":[32],"peganumine":[34],"A.":[35],"The":[36],"latter":[37],"features":[39],"a":[40,66],"protecting-group-free":[41],"assembly":[42],"an":[44],"asymmetric":[45],"disulfonimide-catalyzed":[46],"cyclization.":[47],"Furthermore,":[48],"formal":[49],"syntheses":[50],"hirsutine,":[52],"deplancheine,":[53],"10-desbromoarborescidine":[54],"A,":[55],"oxindole":[57],"rhynchophylline":[59],"isorhynchophylline":[61],"have":[62],"achieved.":[64],"Finally,":[65],"concise":[67],"berberine":[70],"ilicifoline":[72],"B":[73],"was":[74],"completed.":[75]},"counts_by_year":[{"year":2026,"cited_by_count":6},{"year":2025,"cited_by_count":13},{"year":2024,"cited_by_count":10},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":11},{"year":2021,"cited_by_count":4}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2021-03-29T00:00:00"}