{"id":"https://openalex.org/W1975476282","doi":"https://doi.org/10.1021/ol062470p","title":"Thermolysis of Isomigrastatin and Its Congeners via [3,3]-Sigmatropic Rearrangement: A New Route to the Synthesis of Migrastatin and Its Analogues","display_name":"Thermolysis of Isomigrastatin and Its Congeners via [3,3]-Sigmatropic Rearrangement: A New Route to the Synthesis of Migrastatin and Its Analogues","publication_year":2006,"publication_date":"2006-11-11","ids":{"openalex":"https://openalex.org/W1975476282","doi":"https://doi.org/10.1021/ol062470p","mag":"1975476282","pmid":"https://pubmed.ncbi.nlm.nih.gov/17134292","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/2555980"},"language":"en","primary_location":{"id":"doi:10.1021/ol062470p","doi":"https://doi.org/10.1021/ol062470p","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol062470p","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":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2555980","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5028227890","display_name":"Jianhua Ju","orcid":"https://orcid.org/0000-0001-7712-8027","observed_orcids":["https://orcid.org/0000-0001-7712-8027"]},"institutions":[{"id":"https://openalex.org/I135310074","display_name":"University of Wisconsin\u2013Madison","ror":"https://ror.org/01y2jtd41","country_code":"US","type":"education","lineage":["https://openalex.org/I135310074"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jianhua Ju","raw_affiliation_strings":["Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705","institution_ids":["https://openalex.org/I135310074"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5103397400","display_name":"Si\u2010Kyu Lim","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135310074","display_name":"University of Wisconsin\u2013Madison","ror":"https://ror.org/01y2jtd41","country_code":"US","type":"education","lineage":["https://openalex.org/I135310074"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Si-Kyu Lim","raw_affiliation_strings":["Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705","institution_ids":["https://openalex.org/I135310074"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100742764","display_name":"Hui Jiang","orcid":"https://orcid.org/0000-0002-4534-1322","observed_orcids":["https://orcid.org/0000-0002-4534-1322"]},"institutions":[{"id":"https://openalex.org/I135310074","display_name":"University of Wisconsin\u2013Madison","ror":"https://ror.org/01y2jtd41","country_code":"US","type":"education","lineage":["https://openalex.org/I135310074"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Hui Jiang","raw_affiliation_strings":["Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705","institution_ids":["https://openalex.org/I135310074"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111647545","display_name":"Jeong\u2010Woo Seo","orcid":"https://orcid.org/0009-0008-4811-4820","observed_orcids":["https://orcid.org/0009-0008-4811-4820"]},"institutions":[{"id":"https://openalex.org/I135310074","display_name":"University of Wisconsin\u2013Madison","ror":"https://ror.org/01y2jtd41","country_code":"US","type":"education","lineage":["https://openalex.org/I135310074"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jeong-Woo Seo","raw_affiliation_strings":["Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705","institution_ids":["https://openalex.org/I135310074"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5069137009","display_name":"Yeng Her","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I135310074","display_name":"University of Wisconsin\u2013Madison","ror":"https://ror.org/01y2jtd41","country_code":"US","type":"education","lineage":["https://openalex.org/I135310074"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Yeng Her","raw_affiliation_strings":["Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705","institution_ids":["https://openalex.org/I135310074"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5087514362","display_name":"Ben Shen","orcid":"https://orcid.org/0000-0002-9750-5982","observed_orcids":["https://orcid.org/0000-0002-9750-5982"]},"institutions":[{"id":"https://openalex.org/I135310074","display_name":"University of Wisconsin\u2013Madison","ror":"https://ror.org/01y2jtd41","country_code":"US","type":"education","lineage":["https://openalex.org/I135310074"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Ben Shen","raw_affiliation_strings":["Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, and Department of Chemistry, University of Wisconsin\u2212Madison, Madison, Wisconsin 53705","institution_ids":["https://openalex.org/I135310074"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I135310074"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.8021,"has_fulltext":false,"cited_by_count":28,"citation_normalized_percentile":{"value":0.82306519,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"8","issue":"25","first_page":"5865","last_page":"5868"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13876","display_name":"Chemical synthesis and pharmacological studies","score":0.3345000147819519,"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/T13876","display_name":"Chemical synthesis and pharmacological studies","score":0.3345000147819519,"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":0.26100000739097595,"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/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.16990000009536743,"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/3-3-sigmatropic-rearrangement","display_name":"[3,3]-sigmatropic rearrangement","score":0.921999990940094},{"id":"https://openalex.org/keywords/thermal-decomposition","display_name":"thermal decomposition","score":0.9120000004768372},{"id":"https://openalex.org/keywords/ring-expansion","display_name":"ring expansion","score":0.9670000076293945},{"id":"https://openalex.org/keywords/enantiospecific-synthesis","display_name":"enantiospecific synthesis","score":0.8230000138282776},{"id":"https://openalex.org/keywords/heterocycle-synthesis","display_name":"heterocyclic synthesis","score":0.40299999713897705}],"concepts":[{"id":"https://openalex.org/C58590140","wikidata":"https://www.wikidata.org/wiki/Q306614","display_name":"Sigmatropic reaction","level":2,"score":0.9287376403808594},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.886023998260498},{"id":"https://openalex.org/C160434732","wikidata":"https://www.wikidata.org/wiki/Q2611095","display_name":"Thermal decomposition","level":2,"score":0.7119240164756775},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.5633716583251953},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4396851062774658},{"id":"https://openalex.org/C2776138744","wikidata":"https://www.wikidata.org/wiki/Q898367","display_name":"Rearrangement reaction","level":3,"score":0.437100887298584},{"id":"https://openalex.org/C96350342","wikidata":"https://www.wikidata.org/wiki/Q905087","display_name":"Cope rearrangement","level":2,"score":0.4180000424385071},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.39577919244766235},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.358731210231781},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3558385372161865},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2634892761707306},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.12918463349342346}],"mesh":[{"descriptor_ui":"D002851","descriptor_name":"Chromatography, High Pressure Liquid","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006358","descriptor_name":"Hot Temperature","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007536","descriptor_name":"Isomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007783","descriptor_name":"Lactones","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D007783","descriptor_name":"Lactones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010881","descriptor_name":"Piperidones","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D010881","descriptor_name":"Piperidones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013058","descriptor_name":"Mass Spectrometry","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":"D018942","descriptor_name":"Macrolides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D018942","descriptor_name":"Macrolides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":3,"locations":[{"id":"doi:10.1021/ol062470p","doi":"https://doi.org/10.1021/ol062470p","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol062470p","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:17134292","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/17134292","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"},{"id":"pmh:oai:pubmedcentral.nih.gov:2555980","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2555980","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":"Org Lett","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:2555980","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2555980","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":"Org Lett","raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G141094016","display_name":null,"funder_award_id":"CA106150","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G1805831874","display_name":"UWCCC National Cooperative Drug Discovery Group for Can*","funder_award_id":"U19CA113297","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G2271657281","display_name":null,"funder_award_id":"CA113297","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G5977718968","display_name":null,"funder_award_id":"AI51689","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"},{"id":"https://openalex.org/G5982549630","display_name":"Enediyne Antitumor Antibiotic Synthesis - Streptomycetes","funder_award_id":"K02AI051689","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"},{"id":"https://openalex.org/G701551177","display_name":"AT-less Type I Polyketide Synthases","funder_award_id":"R01CA106150","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"}],"funders":[{"id":"https://openalex.org/F4320337351","display_name":"National Cancer Institute","ror":"https://ror.org/040gcmg81"},{"id":"https://openalex.org/F4320337355","display_name":"National Institute of Allergy and Infectious Diseases","ror":"https://ror.org/043z4tv69"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":13,"referenced_works":["https://openalex.org/W1966438414","https://openalex.org/W1984878981","https://openalex.org/W1993594425","https://openalex.org/W1997453147","https://openalex.org/W2000469215","https://openalex.org/W2048404184","https://openalex.org/W2053317505","https://openalex.org/W2081347927","https://openalex.org/W2115552487","https://openalex.org/W2135767836","https://openalex.org/W2139588238","https://openalex.org/W2334777282","https://openalex.org/W4255941290"],"related_works":["https://openalex.org/W2036631554","https://openalex.org/W2132507626","https://openalex.org/W2499421004","https://openalex.org/W2086870583","https://openalex.org/W1966321525","https://openalex.org/W2067688139","https://openalex.org/W1491935025","https://openalex.org/W2014891305","https://openalex.org/W2142861794","https://openalex.org/W804385684"],"abstract_inverted_index":{"Thermolysis":[0],"of":[1,34,52],"isomigrastatin":[2,42],"(1)":[3],"under":[4],"neat":[5],"heating":[6],"conditions":[7],"afforded":[8],"migrastatin":[9,53],"(1a).":[10],"The":[11,31],"reaction":[12,36],"is":[13,26],"proposed":[14],"to":[15,49],"proceed":[16],"via":[17],"a":[18,46],"concerted":[19],"[3,3]-sigmatropic":[20],"rearrangement":[21],"by":[22],"which":[23],"ring":[24],"expansion":[25],"achieved":[27],"regio-":[28],"and":[29],"enantiospecifically.":[30],"general":[32],"applicability":[33],"this":[35],"was":[37],"demonstrated":[38],"with":[39],"six":[40],"additional":[41],"congeners":[43],"(3-8),":[44],"providing":[45],"new":[47],"route":[48],"the":[50],"synthesis":[51],"analogues":[54],"(3a-8a).":[55],"[reaction:":[56],"see":[57],"text]":[58]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":3},{"year":2015,"cited_by_count":2},{"year":2013,"cited_by_count":4}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
