{"id":"https://openalex.org/W2074882464","doi":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","title":"The First Asymmetric Total Synthesis of Tetrodotoxin, a Puffer Fish Toxin","display_name":"The First Asymmetric Total Synthesis of Tetrodotoxin, a Puffer Fish Toxin","publication_year":2007,"publication_date":"2007-01-01","ids":{"openalex":"https://openalex.org/W2074882464","doi":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","mag":"2074882464"},"language":"en","primary_location":{"id":"doi:10.5059/yukigoseikyokaishi.65.492","doi":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","is_oa":true,"landing_page_url":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","pdf_url":"https://www.jstage.jst.go.jp/article/yukigoseikyokaishi1943/65/5/65_5_492/_pdf","source":{"id":"https://openalex.org/S4210185993","display_name":"Journal of Synthetic Organic Chemistry Japan","issn_l":"0037-9980","issn":["0037-9980","1883-6526"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1","poland-20","russia-white-list-4"],"host_organization":"https://openalex.org/P4310313446","host_organization_name":"Society of Synthetic Organic Chemistry, Japan","host_organization_lineage":["https://openalex.org/P4310313446"],"host_organization_lineage_names":["Society of Synthetic Organic Chemistry, Japan"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Synthetic Organic Chemistry, Japan","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":true,"oa_status":"bronze","oa_url":"https://www.jstage.jst.go.jp/article/yukigoseikyokaishi1943/65/5/65_5_492/_pdf","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5102825159","display_name":"Minoru Isobe","orcid":"https://orcid.org/0000-0002-5244-3300","observed_orcids":["https://orcid.org/0000-0002-5244-3300","https://orcid.org/0009-0008-3489-2322"]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Minoru Isobe","raw_affiliation_strings":["Graduate School of Bioagricultural Science and School of Agricultural Sciences, Nagoya University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Graduate School of Bioagricultural Science and School of Agricultural Sciences, Nagoya University","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5042859239","display_name":"Norio Ohyabu","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I44892455","display_name":"Takeda (Japan)","ror":"https://ror.org/04hjbmv12","country_code":"JP","type":"company","lineage":["https://openalex.org/I44892455"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Norio Ohyabu","raw_affiliation_strings":["\u6b66\u7530\u85ac\u54c1\u5de5\u696d\u682a\u5f0f\u4f1a\u793e\u533b\u85ac\u7814\u7a76\u672c\u90e8\u5316\u5b66\u7814\u7a76\u6240"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"\u6b66\u7530\u85ac\u54c1\u5de5\u696d\u682a\u5f0f\u4f1a\u793e\u533b\u85ac\u7814\u7a76\u672c\u90e8\u5316\u5b66\u7814\u7a76\u6240","institution_ids":["https://openalex.org/I44892455"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5016225060","display_name":"Toshio Nishikawa","orcid":"https://orcid.org/0000-0003-1955-6618","observed_orcids":["https://orcid.org/0000-0003-1955-6618"]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Toshio Nishikawa","raw_affiliation_strings":["Graduate School of Bioagricultural Science and School of Agricultural Sciences, Nagoya University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Graduate School of Bioagricultural Science and School of Agricultural Sciences, Nagoya University","institution_ids":["https://openalex.org/I60134161"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":0.682,"has_fulltext":true,"cited_by_count":8,"citation_normalized_percentile":{"value":0.62662383,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":87,"max":95},"biblio":{"volume":"65","issue":"5","first_page":"492","last_page":"501"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.4417000114917755,"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":0.4417000114917755,"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":0.35670000314712524,"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":0.11339999735355377,"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/tetrodotoxin","display_name":"tetrodotoxin","score":1.0},{"id":"https://openalex.org/keywords/asymmetric-total-synthesis","display_name":"asymmetric total synthesis","score":0.9950000047683716},{"id":"https://openalex.org/keywords/marine-natural-products","display_name":"marine natural products","score":0.8159999847412109},{"id":"https://openalex.org/keywords/intramolecular-aldol-condensation","display_name":"intramolecular aldol condensation","score":0.9639999866485596},{"id":"https://openalex.org/keywords/sonogashira-coupling","display_name":"Sonogashira coupling","score":0.9419999718666077},{"id":"https://openalex.org/keywords/claisen-rearrangement","display_name":"Claisen rearrangement","score":0.9940000176429749},{"id":"https://openalex.org/keywords/regioselective-hydroxylation","display_name":"regioselective hydroxylation","score":0.902999997138977},{"id":"https://openalex.org/keywords/intramolecular-conjugate-addition","display_name":"intramolecular conjugate addition","score":0.859000027179718},{"id":"https://openalex.org/keywords/overman-rearrangement","display_name":"Overman rearrangement","score":0.7979999780654907},{"id":"https://openalex.org/keywords/epoxide-ring-opening","display_name":"epoxide ring opening","score":0.7910000085830688},{"id":"https://openalex.org/keywords/guanidinylation","display_name":"guanidinylation","score":0.8650000095367432},{"id":"https://openalex.org/keywords/enantiomerically-pure-synthesis","display_name":"enantiomerically pure synthesis","score":0.6340000033378601}],"concepts":[{"id":"https://openalex.org/C2776568683","wikidata":"https://www.wikidata.org/wiki/Q23005640","display_name":"Moiety","level":2,"score":0.7217710018157959},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6987826824188232},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.6057325005531311},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5946305990219116},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.5273711681365967},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.5199497938156128},{"id":"https://openalex.org/C18616679","wikidata":"https://www.wikidata.org/wiki/Q1027170","display_name":"Aldol condensation","level":3,"score":0.5059399008750916},{"id":"https://openalex.org/C2777738585","wikidata":"https://www.wikidata.org/wiki/Q170744","display_name":"Ketone","level":2,"score":0.4830108880996704},{"id":"https://openalex.org/C61156836","wikidata":"https://www.wikidata.org/wiki/Q494392","display_name":"Aldol reaction","level":3,"score":0.4631703495979309},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.31471556425094604},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.5059/yukigoseikyokaishi.65.492","doi":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","is_oa":true,"landing_page_url":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","pdf_url":"https://www.jstage.jst.go.jp/article/yukigoseikyokaishi1943/65/5/65_5_492/_pdf","source":{"id":"https://openalex.org/S4210185993","display_name":"Journal of Synthetic Organic Chemistry Japan","issn_l":"0037-9980","issn":["0037-9980","1883-6526"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1","poland-20","russia-white-list-4"],"host_organization":"https://openalex.org/P4310313446","host_organization_name":"Society of Synthetic Organic Chemistry, Japan","host_organization_lineage":["https://openalex.org/P4310313446"],"host_organization_lineage_names":["Society of Synthetic Organic Chemistry, Japan"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Synthetic Organic Chemistry, Japan","raw_type":"journal-article"}],"best_oa_location":{"id":"doi:10.5059/yukigoseikyokaishi.65.492","doi":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","is_oa":true,"landing_page_url":"https://doi.org/10.5059/yukigoseikyokaishi.65.492","pdf_url":"https://www.jstage.jst.go.jp/article/yukigoseikyokaishi1943/65/5/65_5_492/_pdf","source":{"id":"https://openalex.org/S4210185993","display_name":"Journal of Synthetic Organic Chemistry Japan","issn_l":"0037-9980","issn":["0037-9980","1883-6526"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","norway-1","poland-20","russia-white-list-4"],"host_organization":"https://openalex.org/P4310313446","host_organization_name":"Society of Synthetic Organic Chemistry, Japan","host_organization_lineage":["https://openalex.org/P4310313446"],"host_organization_lineage_names":["Society of Synthetic Organic Chemistry, Japan"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Synthetic Organic Chemistry, Japan","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W2074882464.pdf","grobid_xml":"https://content.openalex.org/works/W2074882464.grobid-xml"},"referenced_works_count":7,"referenced_works":["https://openalex.org/W598727736","https://openalex.org/W1969129051","https://openalex.org/W2049076058","https://openalex.org/W6600158986","https://openalex.org/W6600672703","https://openalex.org/W6603677382","https://openalex.org/W6823962751"],"related_works":["https://openalex.org/W1999989556","https://openalex.org/W2091067204","https://openalex.org/W2135955454","https://openalex.org/W2170976556","https://openalex.org/W2471045209","https://openalex.org/W1978315463","https://openalex.org/W3174713013","https://openalex.org/W2009100306","https://openalex.org/W4391140814","https://openalex.org/W2574006542"],"abstract_inverted_index":{"Tetrodotoxin,":[0],"a":[1,39,57,71,156],"toxic":[2],"principle":[3],"of":[4,10,18,70,89,94,109,128,133,151,167],"puffer":[5],"fish":[6],"poisoning,":[7],"is":[8],"one":[9],"the":[11,19,28,33,48,98,115,134,152,164],"most":[12],"famous":[13],"marine":[14],"natural":[15],"products":[16],"because":[17],"complex":[20],"structure":[21,29],"and":[22,86,146],"its":[23],"potent":[24],"biological":[25],"activity.":[26],"Since":[27,92],"elucidation":[30],"in":[31,169],"1964,":[32],"toxin":[34],"has":[35],"been":[36],"recognized":[37],"as":[38,56,143],"formidable":[40],"target":[41],"molecule":[42],"for":[43,114],"total":[44,51,165],"synthesis.":[45],"We":[46],"achieved":[47],"first":[49],"asymmetric":[50],"synthesis":[52,166],"commencing":[53],"from":[54],"2-acetoxy-tri-O-acetyl-D-glucal":[55],"chiral":[58],"starting":[59],"material.":[60],"Highly":[61],"hydroxylated":[62],"cyclohexane":[63],"was":[64,79,102,121,140],"constructed":[65],"by":[66,97,123,131,149],"intramolecular":[67,106],"aldol":[68],"condensation":[69],"precursor":[72],"having":[73],"methyl":[74],"ketone":[75],"with":[76,126],"dihydroxyacetone,":[77],"which":[78],"synthesized":[80,122],"through":[81],"Sonogashira":[82],"coupling,":[83],"Claisen":[84],"rearrangement":[85,101],"regioselective":[87],"hydroxylations":[88],"acetone":[90],"moiety.":[91],"installation":[93],"nitrogen":[95],"functionality":[96],"attempted":[99],"Overman":[100],"unsuccessful,":[103],"we":[104],"employed":[105],"conjugate":[107],"addition":[108],"carbamate":[110],"to":[111],"unsaturated":[112],"ester":[113],"purpose.":[116],"The":[117,138],"\u03b1-hydroxyl":[118],"lactone":[119,139],"moiety":[120],"epoxide":[124],"opening":[125],"enolate":[127],"aldehyde":[129],"followed":[130,148],"oxidation-reduction":[132],"resulting":[135],"cyclic":[136],"vinylether.":[137],"then":[141],"protected":[142,158],"ortho":[144],"ester,":[145],"guanidinylation":[147],"cleavage":[150],"1,":[153],"2-glycol":[154],"gave":[155],"fully":[157],"tetrodotoxin.":[159],"Protective":[160],"group":[161],"elaboration":[162],"furnished":[163],"tetrodotoxin":[168],"an":[170],"enantiomerically":[171],"pure":[172],"form.":[173]},"counts_by_year":[{"year":2021,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2013,"cited_by_count":2}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
