{"id":"https://openalex.org/W2015660728","doi":"https://doi.org/10.1021/ja710485n","title":"Total Synthesis of the Originally Proposed and Revised Structures of Palmerolide A and Isomers Thereof","display_name":"Total Synthesis of the Originally Proposed and Revised Structures of Palmerolide A and Isomers Thereof","publication_year":2008,"publication_date":"2008-02-26","ids":{"openalex":"https://openalex.org/W2015660728","doi":"https://doi.org/10.1021/ja710485n","mag":"2015660728","pmid":"https://pubmed.ncbi.nlm.nih.gov/18298117"},"language":"en","primary_location":{"id":"doi:10.1021/ja710485n","doi":"https://doi.org/10.1021/ja710485n","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja710485n","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":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5065008454","display_name":"Kyriacos Costa Nicolaou","orcid":"https://orcid.org/0000-0001-5332-2511","observed_orcids":["https://orcid.org/0000-0001-5332-2511"]},"institutions":[{"id":"https://openalex.org/I115228651","display_name":"Agency for Science, Technology and Research","ror":"https://ror.org/036wvzt09","country_code":"SG","type":"government","lineage":["https://openalex.org/I115228651"]},{"id":"https://openalex.org/I4210105704","display_name":"Institute of Chemical and Engineering Sciences","ror":"https://ror.org/01cbwn720","country_code":"SG","type":"facility","lineage":["https://openalex.org/I115228651","https://openalex.org/I4210105704","https://openalex.org/I91275662"]}],"countries":["SG"],"is_corresponding":false,"raw_author_name":"K. C. Nicolaou","raw_affiliation_strings":["Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667","institution_ids":["https://openalex.org/I115228651","https://openalex.org/I4210105704"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5101449585","display_name":"Ya\u2010Ping Sun","orcid":"https://orcid.org/0000-0003-0633-6253","observed_orcids":["https://orcid.org/0000-0003-0633-6253"]},"institutions":[{"id":"https://openalex.org/I115228651","display_name":"Agency for Science, Technology and Research","ror":"https://ror.org/036wvzt09","country_code":"SG","type":"government","lineage":["https://openalex.org/I115228651"]},{"id":"https://openalex.org/I4210105704","display_name":"Institute of Chemical and Engineering Sciences","ror":"https://ror.org/01cbwn720","country_code":"SG","type":"facility","lineage":["https://openalex.org/I115228651","https://openalex.org/I4210105704","https://openalex.org/I91275662"]}],"countries":["SG"],"is_corresponding":false,"raw_author_name":"Ya-Ping Sun","raw_affiliation_strings":["Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667","institution_ids":["https://openalex.org/I115228651","https://openalex.org/I4210105704"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5078038431","display_name":"Ramakrishna Guduru","orcid":"https://orcid.org/0000-0001-5091-0596","observed_orcids":["https://orcid.org/0000-0001-5091-0596"]},"institutions":[{"id":"https://openalex.org/I115228651","display_name":"Agency for Science, Technology and Research","ror":"https://ror.org/036wvzt09","country_code":"SG","type":"government","lineage":["https://openalex.org/I115228651"]},{"id":"https://openalex.org/I4210105704","display_name":"Institute of Chemical and Engineering Sciences","ror":"https://ror.org/01cbwn720","country_code":"SG","type":"facility","lineage":["https://openalex.org/I115228651","https://openalex.org/I4210105704","https://openalex.org/I91275662"]}],"countries":["SG"],"is_corresponding":false,"raw_author_name":"Ramakrishna Guduru","raw_affiliation_strings":["Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667","institution_ids":["https://openalex.org/I115228651","https://openalex.org/I4210105704"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5017415148","display_name":"Biswadip Banerji","orcid":"https://orcid.org/0000-0001-9898-253X","observed_orcids":["https://orcid.org/0000-0001-9898-253X"]},"institutions":[{"id":"https://openalex.org/I115228651","display_name":"Agency for Science, Technology and Research","ror":"https://ror.org/036wvzt09","country_code":"SG","type":"government","lineage":["https://openalex.org/I115228651"]},{"id":"https://openalex.org/I4210105704","display_name":"Institute of Chemical and Engineering Sciences","ror":"https://ror.org/01cbwn720","country_code":"SG","type":"facility","lineage":["https://openalex.org/I115228651","https://openalex.org/I4210105704","https://openalex.org/I91275662"]}],"countries":["SG"],"is_corresponding":false,"raw_author_name":"Biswadip Banerji","raw_affiliation_strings":["Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667","institution_ids":["https://openalex.org/I115228651","https://openalex.org/I4210105704"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5027806941","display_name":"David Y.\u2010K. Chen","orcid":"https://orcid.org/0000-0001-8782-3090","observed_orcids":["https://orcid.org/0000-0001-8782-3090"]},"institutions":[{"id":"https://openalex.org/I115228651","display_name":"Agency for Science, Technology and Research","ror":"https://ror.org/036wvzt09","country_code":"SG","type":"government","lineage":["https://openalex.org/I115228651"]},{"id":"https://openalex.org/I4210105704","display_name":"Institute of Chemical and Engineering Sciences","ror":"https://ror.org/01cbwn720","country_code":"SG","type":"facility","lineage":["https://openalex.org/I115228651","https://openalex.org/I4210105704","https://openalex.org/I91275662"]}],"countries":["SG"],"is_corresponding":false,"raw_author_name":"David Y.-K. Chen","raw_affiliation_strings":["Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667","institution_ids":["https://openalex.org/I115228651","https://openalex.org/I4210105704"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":5.9602,"has_fulltext":false,"cited_by_count":133,"citation_normalized_percentile":{"value":0.97227938,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":100},"biblio":{"volume":"130","issue":"11","first_page":"3633","last_page":"3644"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11549","display_name":"Synthetic Organic Chemistry Methods","score":0.6723999977111816,"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/T11549","display_name":"Synthetic Organic Chemistry Methods","score":0.6723999977111816,"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":0.15469999611377716,"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/T13221","display_name":"Biological Activity of Diterpenoids and Biflavonoids","score":0.06669999659061432,"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/total-synthesis","display_name":"total synthesis","score":0.9570000171661377},{"id":"https://openalex.org/keywords/stereoisomers","display_name":"stereoisomers","score":0.8169999718666077},{"id":"https://openalex.org/keywords/marine-natural-products","display_name":"marine natural products","score":0.8109999895095825},{"id":"https://openalex.org/keywords/structure-revision","display_name":"structure revision","score":0.6740000247955322},{"id":"https://openalex.org/keywords/melanoma","display_name":"melanoma","score":0.6159999966621399},{"id":"https://openalex.org/keywords/macrocyclization","display_name":"macrocyclization","score":0.652999997138977},{"id":"https://openalex.org/keywords/ring-closing-metathesis","display_name":"ring-closing metathesis","score":0.9789999723434448},{"id":"https://openalex.org/keywords/horner-wadsworth-emmons-olefination","display_name":"Horner-Wadsworth-Emmons olefination","score":0.9779999852180481},{"id":"https://openalex.org/keywords/stille-coupling","display_name":"Stille coupling","score":0.8610000014305115},{"id":"https://openalex.org/keywords/copper-catalyzed-coupling","display_name":"copper-catalyzed coupling","score":0.859000027179718},{"id":"https://openalex.org/keywords/enamides","display_name":"enamides","score":0.6240000128746033},{"id":"https://openalex.org/keywords/convergent-synthesis","display_name":"convergent synthesis","score":0.6779999732971191}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9789338111877441},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.46326711773872375},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.39396756887435913},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.35236650705337524}],"mesh":[{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","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":2,"locations":[{"id":"doi:10.1021/ja710485n","doi":"https://doi.org/10.1021/ja710485n","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja710485n","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:18298117","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/18298117","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":17,"referenced_works":["https://openalex.org/W1963591519","https://openalex.org/W1964191028","https://openalex.org/W1980947232","https://openalex.org/W1986193108","https://openalex.org/W1986917711","https://openalex.org/W2004828453","https://openalex.org/W2022412731","https://openalex.org/W2027026672","https://openalex.org/W2028943451","https://openalex.org/W2031799240","https://openalex.org/W2037242455","https://openalex.org/W2047690315","https://openalex.org/W2049889506","https://openalex.org/W2084841082","https://openalex.org/W2099571918","https://openalex.org/W2104168237","https://openalex.org/W2160373896"],"related_works":["https://openalex.org/W2153048735","https://openalex.org/W2170572394","https://openalex.org/W1966049487","https://openalex.org/W2153616484","https://openalex.org/W644348601","https://openalex.org/W3043406629","https://openalex.org/W2093225447","https://openalex.org/W2163184027","https://openalex.org/W2316297849","https://openalex.org/W1981312458"],"abstract_inverted_index":{"Palmerolide":[0],"A":[1,31],"is":[2],"a":[3,131,149],"recently":[4],"disclosed":[5],"marine":[6],"natural":[7],"product":[8],"possessing":[9],"striking":[10],"biological":[11],"properties,":[12],"including":[13,33],"potent":[14],"and":[15,38,49,70,72,75,96,120,127],"selective":[16],"activity":[17],"against":[18],"the":[19,34,39,57,78,82,85,88,102,107,111,114,121,135,145],"melanoma":[20],"cancer":[21],"cell":[22],"line":[23],"UACC-62.":[24],"The":[25,46,117,138],"total":[26],"syntheses":[27,55,139],"of":[28,59,84,110,113,144],"five":[29],"palmerolide":[30,115,136],"stereoisomers,":[32],"originally":[35],"proposed":[36],"(1)":[37],"revised":[40],"[ent-(19-epi-20-epi-1)]":[41],"structures,":[42],"have":[43],"been":[44],"accomplished.":[45],"highly":[47],"convergent":[48],"flexible":[50],"strategy":[51],"developed":[52],"for":[53,106],"these":[54],"involved":[56],"construction":[58],"key":[60],"building":[61,86],"blocks":[62],"2,":[63],"19-epi-2,":[64],"20-epi-2,":[65],"ent-2,":[66],"3,":[67],"ent-3,":[68],"4,":[69],"ent-4,":[71],"their":[73],"assembly":[74],"elaboration":[76],"to":[77,133],"target":[79],"compounds.":[80],"For":[81],"union":[83],"blocks,":[87],"Stille":[89],"coupling":[90,151],"reaction,":[91],"Yamaguchi":[92,122],"esterification,":[93],"Horner-Wadsworth-Emmons":[94,118],"olefination,":[95],"ring-closing":[97],"metathesis":[98],"reaction":[99],"were":[100,124,140],"employed,":[101],"latter":[103],"being":[104],"crucial":[105],"stereoselective":[108],"formation":[109],"macrocycle":[112],"structure.":[116],"olefination":[119],"lactonization":[123],"also":[125],"investigated":[126],"found":[128],"successful":[129],"as":[130],"means":[132],"construct":[134],"macrocycle.":[137],"completed":[141],"by":[142],"attachment":[143],"enamide":[146],"moiety":[147],"through":[148],"copper-catalyzed":[150],"process.":[152]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":3},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":7},{"year":2020,"cited_by_count":7},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":3},{"year":2017,"cited_by_count":9},{"year":2016,"cited_by_count":6},{"year":2015,"cited_by_count":7},{"year":2014,"cited_by_count":14},{"year":2013,"cited_by_count":14},{"year":2012,"cited_by_count":14}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
