{"id":"https://openalex.org/W2016563351","doi":"https://doi.org/10.1021/ol035797o","title":"Enantioselective Total Synthesis of (+)-Leucascandrolide A Macrolactone","display_name":"Enantioselective Total Synthesis of (+)-Leucascandrolide A Macrolactone","publication_year":2003,"publication_date":"2003-10-29","ids":{"openalex":"https://openalex.org/W2016563351","doi":"https://doi.org/10.1021/ol035797o","mag":"2016563351","pmid":"https://pubmed.ncbi.nlm.nih.gov/14627404"},"language":"en","primary_location":{"id":"doi:10.1021/ol035797o","doi":"https://doi.org/10.1021/ol035797o","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol035797o","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","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/A5064513319","display_name":"Michael T. Crimmins","orcid":"https://orcid.org/0000-0003-0313-6010","observed_orcids":["https://orcid.org/0000-0003-0313-6010"]},"institutions":[{"id":"https://openalex.org/I114027177","display_name":"University of North Carolina at Chapel Hill","ror":"https://ror.org/0130frc33","country_code":"US","type":"education","lineage":["https://openalex.org/I114027177"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Michael T. Crimmins","raw_affiliation_strings":["Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599","Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, USA. crimmins@email.unc.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599","institution_ids":["https://openalex.org/I114027177"]},{"raw_affiliation_string":"Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, USA. crimmins@email.unc.edu","institution_ids":["https://openalex.org/I114027177"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5032980474","display_name":"Phieng Siliphaivanh","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I114027177","display_name":"University of North Carolina at Chapel Hill","ror":"https://ror.org/0130frc33","country_code":"US","type":"education","lineage":["https://openalex.org/I114027177"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Phieng Siliphaivanh","raw_affiliation_strings":["Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599","institution_ids":["https://openalex.org/I114027177"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I114027177"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":4.4745,"has_fulltext":false,"cited_by_count":69,"citation_normalized_percentile":{"value":0.95219491,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"5","issue":"24","first_page":"4641","last_page":"4644"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.42480000853538513,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.42480000853538513,"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":0.30489999055862427,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.23800000548362732,"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/macrolactones","display_name":"macrolactones","score":0.8519999980926514},{"id":"https://openalex.org/keywords/asymmetric-total-synthesis","display_name":"asymmetric total synthesis","score":0.9670000076293945},{"id":"https://openalex.org/keywords/natural-product-synthesis","display_name":"natural product synthesis","score":0.5929999947547913},{"id":"https://openalex.org/keywords/1-3-propanediol","display_name":"1,3-propanediol","score":0.8679999709129333},{"id":"https://openalex.org/keywords/boron-enolates","display_name":"boron enolates","score":0.9419999718666077}],"concepts":[{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.9480155110359192},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9081957340240479},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.6377755403518677},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4863782227039337},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.33305609226226807},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.27136558294296265},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.13398972153663635}],"mesh":[{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D007659","descriptor_name":"Ketones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D012717","descriptor_name":"Sesquiterpenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D012717","descriptor_name":"Sesquiterpenes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ol035797o","doi":"https://doi.org/10.1021/ol035797o","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol035797o","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:14627404","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/14627404","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G8886871735","display_name":"Asymmetric Synthesis of Antitumor Agents","funder_award_id":"R01CA063572","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"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":9,"referenced_works":["https://openalex.org/W1974120360","https://openalex.org/W2022412731","https://openalex.org/W2041769371","https://openalex.org/W2051780418","https://openalex.org/W2070061941","https://openalex.org/W2316577302","https://openalex.org/W2332216278","https://openalex.org/W2949328027","https://openalex.org/W2951970435"],"related_works":["https://openalex.org/W2076226581","https://openalex.org/W2949912575","https://openalex.org/W4232144140","https://openalex.org/W2010673784","https://openalex.org/W2150486847","https://openalex.org/W2951580450","https://openalex.org/W2004854283","https://openalex.org/W2952561426","https://openalex.org/W4324303420","https://openalex.org/W2952011337"],"abstract_inverted_index":{"[reaction:":[0],"see":[1],"text]":[2],"The":[3,20],"enantioselective":[4],"synthesis":[5,25],"of":[6,30,44,48,64],"the":[7,24,36,45,62,65],"(+)-leucascandrolide":[8],"A":[9],"macrolactone":[10],"has":[11],"been":[12],"achieved":[13],"in":[14,23,55],"20":[15],"linear":[16],"steps":[17,22],"from":[18],"1,3-propanediol.":[19],"key":[21],"are":[26],"a":[27,41,58],"reductive":[28],"cleavage":[29],"bicyclic":[31],"ketal":[32],"5":[33],"to":[34,52],"establish":[35],"C15":[37],"stereogenic":[38],"center":[39],"and":[40],"diastereoselective":[42],"aldol":[43],"boron":[46],"enolate":[47],"methyl":[49],"ketone":[50],"3":[51],"aldehyde":[53],"4":[54],"preparation":[56],"for":[57,61],"heteroconjugate":[59],"addition":[60],"introduction":[63],"C3":[66],"stereocenter.":[67]},"counts_by_year":[{"year":2023,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":2},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":3}],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2016-06-24T00:00:00"}