{"id":"https://openalex.org/W2988910489","doi":"https://doi.org/10.1021/acs.joc.9b02378","title":"Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid","display_name":"Asymmetric Total Synthesis of 19,20-Epoxydocosapentaenoic Acid, a Bioactive Metabolite of Docosahexaenoic Acid","publication_year":2019,"publication_date":"2019-11-08","ids":{"openalex":"https://openalex.org/W2988910489","doi":"https://doi.org/10.1021/acs.joc.9b02378","mag":"2988910489","pmid":"https://pubmed.ncbi.nlm.nih.gov/31701741","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/7944941"},"language":"en","primary_location":{"id":"doi:10.1021/acs.joc.9b02378","doi":"https://doi.org/10.1021/acs.joc.9b02378","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.9b02378","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":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7944941","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5019924991","display_name":"Maris A. Cinelli","orcid":"https://orcid.org/0000-0002-5887-7038","observed_orcids":["https://orcid.org/0000-0002-5887-7038"]},"institutions":[{"id":"https://openalex.org/I87216513","display_name":"Michigan State University","ror":"https://ror.org/05hs6h993","country_code":"US","type":"education","lineage":["https://openalex.org/I87216513"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Maris A. Cinelli","raw_affiliation_strings":["Department of Pharmacology and Toxicology, Michigan State University, East Lansing, Michigan 48824, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Pharmacology and Toxicology, Michigan State University, East Lansing, Michigan 48824, United States","institution_ids":["https://openalex.org/I87216513"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5064274524","display_name":"Kin Sing Stephen Lee","orcid":"https://orcid.org/0000-0003-4541-3063","observed_orcids":["https://orcid.org/0000-0003-4541-3063"]},"institutions":[{"id":"https://openalex.org/I87216513","display_name":"Michigan State University","ror":"https://ror.org/05hs6h993","country_code":"US","type":"education","lineage":["https://openalex.org/I87216513"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Kin Sing Stephen Lee","raw_affiliation_strings":["Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, United States","Department of Pharmacology and Toxicology, Michigan State University, East Lansing, Michigan 48824, United States"],"raw_orcid":"https://orcid.org/0000-0003-4541-3063","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, United States","institution_ids":["https://openalex.org/I87216513"]},{"raw_affiliation_string":"Department of Pharmacology and Toxicology, Michigan State University, East Lansing, Michigan 48824, United States","institution_ids":["https://openalex.org/I87216513"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5064274524"],"corresponding_institution_ids":["https://openalex.org/I87216513"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":1.1394,"has_fulltext":false,"cited_by_count":14,"citation_normalized_percentile":{"value":0.77101297,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":90,"max":98},"biblio":{"volume":"84","issue":"23","first_page":"15362","last_page":"15372"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10387","display_name":"Fatty Acid Research and Health","score":0.7583000063896179,"subfield":{"id":"https://openalex.org/subfields/2916","display_name":"Nutrition and Dietetics"},"field":{"id":"https://openalex.org/fields/29","display_name":"Nursing"},"domain":{"id":"https://openalex.org/domains/4","display_name":"Health Sciences"}},"topics":[{"id":"https://openalex.org/T10387","display_name":"Fatty Acid Research and Health","score":0.7583000063896179,"subfield":{"id":"https://openalex.org/subfields/2916","display_name":"Nutrition and Dietetics"},"field":{"id":"https://openalex.org/fields/29","display_name":"Nursing"},"domain":{"id":"https://openalex.org/domains/4","display_name":"Health Sciences"}},{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.08910000324249268,"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":0.03779999911785126,"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/asymmetric-total-synthesis","display_name":"asymmetric total synthesis","score":0.9179999828338623},{"id":"https://openalex.org/keywords/docosahexaenoic-acid-metabolites","display_name":"docosahexaenoic acid metabolites","score":0.9319999814033508},{"id":"https://openalex.org/keywords/cytochrome-p450-metabolites","display_name":"cytochrome P450 metabolites","score":0.9240000247955322},{"id":"https://openalex.org/keywords/asymmetric-epoxidation","display_name":"asymmetric epoxidation","score":0.9200000166893005},{"id":"https://openalex.org/keywords/wittig-reaction","display_name":"Wittig reaction","score":0.9819999933242798},{"id":"https://openalex.org/keywords/polyene-synthesis","display_name":"polyene synthesis","score":0.3619999885559082}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9228142499923706},{"id":"https://openalex.org/C93237805","wikidata":"https://www.wikidata.org/wiki/Q5375227","display_name":"Enantiopure drug","level":4,"score":0.7705034017562866},{"id":"https://openalex.org/C24292678","wikidata":"https://www.wikidata.org/wiki/Q909735","display_name":"Wittig reaction","level":2,"score":0.7628328800201416},{"id":"https://openalex.org/C2777477808","wikidata":"https://www.wikidata.org/wiki/Q407595","display_name":"Metabolite","level":2,"score":0.755164384841919},{"id":"https://openalex.org/C2779594873","wikidata":"https://www.wikidata.org/wiki/Q2519471","display_name":"Polyene","level":2,"score":0.749619722366333},{"id":"https://openalex.org/C2777171753","wikidata":"https://www.wikidata.org/wiki/Q423345","display_name":"Docosahexaenoic acid","level":4,"score":0.7312449216842651},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.7038751840591431},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.5718404054641724},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.48791858553886414},{"id":"https://openalex.org/C2781349093","wikidata":"https://www.wikidata.org/wiki/Q17177300","display_name":"Docosapentaenoic acid","level":5,"score":0.4662453532218933},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4473956823348999},{"id":"https://openalex.org/C2776437795","wikidata":"https://www.wikidata.org/wiki/Q756551","display_name":"Quisqualic acid","level":5,"score":0.4325960874557495},{"id":"https://openalex.org/C543025807","wikidata":"https://www.wikidata.org/wiki/Q61476","display_name":"Fatty acid","level":2,"score":0.26987794041633606},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.22246479988098145},{"id":"https://openalex.org/C19038510","wikidata":"https://www.wikidata.org/wiki/Q2005087","display_name":"Polyunsaturated fatty acid","level":3,"score":0.18778187036514282},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.13769587874412537},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.0},{"id":"https://openalex.org/C61174792","wikidata":"https://www.wikidata.org/wiki/Q420510","display_name":"Glutamate receptor","level":3,"score":0.0},{"id":"https://openalex.org/C160268369","wikidata":"https://www.wikidata.org/wiki/Q295251","display_name":"AMPA receptor","level":4,"score":0.0}],"mesh":[{"descriptor_ui":"D003577","descriptor_name":"Cytochrome P-450 Enzyme System","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D003577","descriptor_name":"Cytochrome P-450 Enzyme System","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004281","descriptor_name":"Docosahexaenoic Acids","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004281","descriptor_name":"Docosahexaenoic Acids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.joc.9b02378","doi":"https://doi.org/10.1021/acs.joc.9b02378","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.9b02378","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:31701741","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/31701741","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"},{"id":"pmh:oai:pubmedcentral.nih.gov:7944941","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7944941","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 Org Chem","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:7944941","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7944941","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 Org Chem","raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1088101296","display_name":null,"funder_award_id":"DMS 1761320","funder_id":"https://openalex.org/F4320337380","funder_display_name":"Division of Mathematical Sciences"},{"id":"https://openalex.org/G2062977162","display_name":null,"funder_award_id":"ES 024806","funder_id":"https://openalex.org/F4320337361","funder_display_name":"National Institute of Environmental Health Sciences"},{"id":"https://openalex.org/G7031984929","display_name":"Identifying the receptors of environmentally sensitive epoxy-eicosanoids with AMS","funder_award_id":"R00ES024806","funder_id":"https://openalex.org/F4320337361","funder_display_name":"National Institute of Environmental Health Sciences"}],"funders":[{"id":"https://openalex.org/F4320337361","display_name":"National Institute of Environmental Health Sciences","ror":"https://ror.org/00j4k1h63"},{"id":"https://openalex.org/F4320337380","display_name":"Division of Mathematical Sciences","ror":"https://ror.org/051fftw81"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":24,"referenced_works":["https://openalex.org/W45077054","https://openalex.org/W1616455216","https://openalex.org/W1895267357","https://openalex.org/W1969738573","https://openalex.org/W1999942279","https://openalex.org/W2000994563","https://openalex.org/W2012655434","https://openalex.org/W2033594661","https://openalex.org/W2033810907","https://openalex.org/W2036610375","https://openalex.org/W2038792435","https://openalex.org/W2043421811","https://openalex.org/W2067481239","https://openalex.org/W2077890319","https://openalex.org/W2093438138","https://openalex.org/W2145630011","https://openalex.org/W2168308817","https://openalex.org/W2320675240","https://openalex.org/W2558378310","https://openalex.org/W2758839128","https://openalex.org/W2768051700","https://openalex.org/W2892281655","https://openalex.org/W2949283971","https://openalex.org/W2952644437"],"related_works":["https://openalex.org/W2892281655","https://openalex.org/W4302316252","https://openalex.org/W2013028306","https://openalex.org/W2000994563","https://openalex.org/W2092076522","https://openalex.org/W1972084549","https://openalex.org/W3004800228","https://openalex.org/W2114021571","https://openalex.org/W1999740323","https://openalex.org/W2054766993"],"abstract_inverted_index":{"In":[0],"this":[1],"study,":[2],"we":[3],"report":[4],"the":[5,47,50],"first":[6],"asymmetric":[7,34],"total":[8],"synthesis":[9],"of":[10,21,27,49],"19,20-epoxydocosapentaenoic":[11],"acid":[12],"(19,20-EDP),":[13],"a":[14,24],"naturally":[15],"occurring":[16],"bioactive":[17],"cytochrome":[18],"P450":[19],"metabolite":[20],"docosahexaenoic":[22],"acid,":[23],"major":[25],"constituent":[26],"fish":[28],"oil.":[29],"Our":[30,57],"strategy":[31],"involves":[32],"direct":[33],"epoxidation":[35],"to":[36,46,72],"produce":[37],"an":[38,67],"enantiopure":[39],"\u03b2":[40],"-epoxyaldehyde":[41],"that":[42],"can":[43],"be":[44,66],"appended":[45],"rest":[48],"skipped":[51],"polyene":[52],"core":[53],"by":[54,70],"Wittig":[55],"condensation.":[56],"route":[58],"is":[59],"step-economical":[60],"and":[61,64],"late":[62],"divergent":[63],"could":[65],"appealing":[68],"method":[69],"which":[71],"synthesize":[73],"EDP":[74],"analogues":[75],"for":[76],"biological":[77],"studies.":[78]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":1},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":2},{"year":2020,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2019-11-22T00:00:00"}