{"id":"https://openalex.org/W2033676702","doi":"https://doi.org/10.1021/ol5031537","title":"A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H","display_name":"A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H","publication_year":2014,"publication_date":"2014-12-09","ids":{"openalex":"https://openalex.org/W2033676702","doi":"https://doi.org/10.1021/ol5031537","mag":"2033676702","pmid":"https://pubmed.ncbi.nlm.nih.gov/25489925","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/4275150"},"language":"en","primary_location":{"id":"doi:10.1021/ol5031537","doi":"https://doi.org/10.1021/ol5031537","is_oa":true,"landing_page_url":"https://doi.org/10.1021/ol5031537","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/ol5031537?ref=article_openPDF","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":"other-oa","license_id":"https://openalex.org/licenses/other-oa","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":"hybrid","oa_url":"https://pubs.acs.org/doi/pdf/10.1021/ol5031537?ref=article_openPDF","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5047667741","display_name":"Samantha E. Shockley","orcid":"https://orcid.org/0000-0001-5682-8569","observed_orcids":["https://orcid.org/0000-0001-5682-8569"]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Samantha E. Shockley","raw_affiliation_strings":["California Institute of Technology , , 1200 East California Boulevard, MC 101-20 , , ,","The Warren and Katharine\rSchlinger Laboratory for Chemistry and Chemical Engineering, Division\rof Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"California Institute of Technology , , 1200 East California Boulevard, MC 101-20 , , ,","institution_ids":["https://openalex.org/I122411786"]},{"raw_affiliation_string":"The Warren and Katharine\rSchlinger Laboratory for Chemistry and Chemical Engineering, Division\rof Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States","institution_ids":["https://openalex.org/I122411786"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5021366468","display_name":"Jeffrey C. Holder","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jeffrey C. Holder","raw_affiliation_strings":["California Institute of Technology , , 1200 East California Boulevard, MC 101-20 , , ,","The Warren and Katharine\rSchlinger Laboratory for Chemistry and Chemical Engineering, Division\rof Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"California Institute of Technology , , 1200 East California Boulevard, MC 101-20 , , ,","institution_ids":["https://openalex.org/I122411786"]},{"raw_affiliation_string":"The Warren and Katharine\rSchlinger Laboratory for Chemistry and Chemical Engineering, Division\rof Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States","institution_ids":["https://openalex.org/I122411786"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5064849339","display_name":"Brian M. Stoltz","orcid":"https://orcid.org/0000-0001-9837-1528","observed_orcids":["https://orcid.org/0000-0001-9837-1528"]},"institutions":[{"id":"https://openalex.org/I122411786","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055","country_code":"US","type":"education","lineage":["https://openalex.org/I122411786"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Brian M. Stoltz","raw_affiliation_strings":["California Institute of Technology , , 1200 East California Boulevard, MC 101-20 , , ,","The Warren and Katharine\rSchlinger Laboratory for Chemistry and Chemical Engineering, Division\rof Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"California Institute of Technology , , 1200 East California Boulevard, MC 101-20 , , ,","institution_ids":["https://openalex.org/I122411786"]},{"raw_affiliation_string":"The Warren and Katharine\rSchlinger Laboratory for Chemistry and Chemical Engineering, Division\rof Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States","institution_ids":["https://openalex.org/I122411786"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5064849339"],"corresponding_institution_ids":["https://openalex.org/I122411786"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":{"value":4500,"currency":"USD","value_usd":4500},"fwci":1.9053,"has_fulltext":true,"cited_by_count":41,"citation_normalized_percentile":{"value":0.84017714,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"16","issue":"24","first_page":"6362","last_page":"6365"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9848999977111816,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9848999977111816,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.006599999964237213,"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":0.002099999925121665,"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-conjugate-addition","display_name":"asymmetric conjugate addition","score":0.8450000286102295},{"id":"https://openalex.org/keywords/palladium-ii-catalysts","display_name":"palladium(II) catalysts","score":0.7889999747276306},{"id":"https://openalex.org/keywords/quaternary-stereocenters","display_name":"quaternary stereocenters","score":0.9229999780654907},{"id":"https://openalex.org/keywords/hammett-substituent-constants","display_name":"Hammett substituent constants","score":0.9860000014305115},{"id":"https://openalex.org/keywords/natural-product-synthesis","display_name":"natural product synthesis","score":0.6019999980926514}],"concepts":[{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.9776309728622437},{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.9324252605438232},{"id":"https://openalex.org/C2985598853","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Formal synthesis","level":2,"score":0.8185499310493469},{"id":"https://openalex.org/C197336794","wikidata":"https://www.wikidata.org/wiki/Q5161150","display_name":"Conjugate","level":2,"score":0.8019311428070068},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7694864273071289},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.6353096961975098},{"id":"https://openalex.org/C2777289219","wikidata":"https://www.wikidata.org/wiki/Q7632154","display_name":"Substrate (aquarium)","level":2,"score":0.5709110498428345},{"id":"https://openalex.org/C53105671","wikidata":"https://www.wikidata.org/wiki/Q14777816","display_name":"Rational design","level":2,"score":0.5388301610946655},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4924682080745697},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.48035916686058044},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.25891149044036865},{"id":"https://openalex.org/C171250308","wikidata":"https://www.wikidata.org/wiki/Q11468","display_name":"Nanotechnology","level":1,"score":0.134879469871521},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.06935000419616699},{"id":"https://openalex.org/C127313418","wikidata":"https://www.wikidata.org/wiki/Q1069","display_name":"Geology","level":0,"score":0.0},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0},{"id":"https://openalex.org/C111368507","wikidata":"https://www.wikidata.org/wiki/Q43518","display_name":"Oceanography","level":1,"score":0.0},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004224","descriptor_name":"Diterpenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D004224","descriptor_name":"Diterpenes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010165","descriptor_name":"Palladium","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"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":4,"locations":[{"id":"doi:10.1021/ol5031537","doi":"https://doi.org/10.1021/ol5031537","is_oa":true,"landing_page_url":"https://doi.org/10.1021/ol5031537","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/ol5031537?ref=article_openPDF","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":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},{"id":"pmh:oai:pubmedcentral.nih.gov:4275150","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/4275150","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":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Org Lett","raw_type":"Text"},{"id":"pmid:25489925","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/25489925","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:authors.library.caltech.edu:52799","doi":null,"is_oa":false,"landing_page_url":"https://resolver.caltech.edu/CaltechAUTHORS:20141215-090404543","pdf_url":null,"source":{"id":"https://openalex.org/S4306402161","display_name":"CaltechAUTHORS (California Institute of Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I122411786","host_organization_name":"California Institute of Technology","host_organization_lineage":["https://openalex.org/I122411786"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Article"}],"best_oa_location":{"id":"doi:10.1021/ol5031537","doi":"https://doi.org/10.1021/ol5031537","is_oa":true,"landing_page_url":"https://doi.org/10.1021/ol5031537","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/ol5031537?ref=article_openPDF","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":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1962920509","display_name":"The Synthesis of Bioactive Polycyclic Natural Products","funder_award_id":"R01GM080269","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G426348193","display_name":null,"funder_award_id":"GM080269","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G5902322555","display_name":"400 MHz Nuclear Magnetic Resonance Spectrometer","funder_award_id":"S10RR027690","funder_id":"https://openalex.org/F4320337375","funder_display_name":"National Center for Research Resources"},{"id":"https://openalex.org/G7192793593","display_name":null,"funder_award_id":"RR027690","funder_id":"https://openalex.org/F4320337375","funder_display_name":"National Center for Research Resources"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"},{"id":"https://openalex.org/F4320309398","display_name":"California Institute of Technology","ror":"https://ror.org/05dxps055"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337375","display_name":"National Center for Research Resources","ror":"https://ror.org/04pw6fb54"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W2033676702.pdf","grobid_xml":"https://content.openalex.org/works/W2033676702.grobid-xml"},"referenced_works_count":41,"referenced_works":["https://openalex.org/W1576288888","https://openalex.org/W1587486317","https://openalex.org/W1965395049","https://openalex.org/W1969603340","https://openalex.org/W1970098418","https://openalex.org/W1986230772","https://openalex.org/W1987174312","https://openalex.org/W1990075034","https://openalex.org/W1991613169","https://openalex.org/W2002310711","https://openalex.org/W2003633070","https://openalex.org/W2007191981","https://openalex.org/W2010558976","https://openalex.org/W2011354825","https://openalex.org/W2012529413","https://openalex.org/W2017440728","https://openalex.org/W2017725085","https://openalex.org/W2018823964","https://openalex.org/W2028103151","https://openalex.org/W2031658864","https://openalex.org/W2037599264","https://openalex.org/W2040145503","https://openalex.org/W2040769981","https://openalex.org/W2046042448","https://openalex.org/W2062029963","https://openalex.org/W2067885008","https://openalex.org/W2071818512","https://openalex.org/W2073732573","https://openalex.org/W2074609212","https://openalex.org/W2081030040","https://openalex.org/W2114105210","https://openalex.org/W2160108558","https://openalex.org/W2160790360","https://openalex.org/W2327178621","https://openalex.org/W2335152710","https://openalex.org/W2335371893","https://openalex.org/W2950606165","https://openalex.org/W2951490957","https://openalex.org/W2951715334","https://openalex.org/W2951717815","https://openalex.org/W3005214039"],"related_works":["https://openalex.org/W2012529413","https://openalex.org/W202291361","https://openalex.org/W4411299182","https://openalex.org/W2108148140","https://openalex.org/W3015226549","https://openalex.org/W2126843749","https://openalex.org/W2783246491","https://openalex.org/W2104919717","https://openalex.org/W2167690695","https://openalex.org/W2165365662"],"abstract_inverted_index":{"A":[0],"catalytic,":[1],"enantioselective":[2,58],"formal":[3,69],"synthesis":[4],"of":[5,31,39,44,55,67],"(+)-dichroanone":[6],"and":[7],"(+)-taiwaniaquinone":[8],"H":[9],"is":[10],"reported.":[11],"The":[12,28],"all-carbon":[13],"quaternary":[14],"stereocenter":[15],"was":[16],"constructed":[17],"by":[18,23],"asymmetric":[19],"conjugate":[20,59],"addition":[21,60],"catalyzed":[22],"a":[24,32,40,56],"palladium(II)":[25],"(S)-tert-butylpyridinooxazoline":[26],"complex.":[27],"unexpected":[29],"formation":[30],"[3.2.1]":[33],"bicyclic":[34],"intermediate":[35],"required":[36],"the":[37,45,52,65,68],"identification":[38],"new":[41],"route.":[42],"Analysis":[43],"Hammett":[46],"constants":[47],"for":[48],"para-substituted":[49],"arenes":[50],"enabled":[51],"rational":[53],"design":[54],"highly":[57],"substrate":[61],"that":[62],"led":[63],"to":[64],"completion":[66],"synthesis.":[70]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":3},{"year":2022,"cited_by_count":5},{"year":2021,"cited_by_count":5},{"year":2020,"cited_by_count":5},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":4},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":6},{"year":2015,"cited_by_count":5},{"year":2012,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
