{"id":"https://openalex.org/W2149805101","doi":"https://doi.org/10.1002/anie.200603652","title":"Enantioselective Synthesis of Oasomycin A, Part III: Fragment Assembly and Confirmation of Structure","display_name":"Enantioselective Synthesis of Oasomycin A, Part III: Fragment Assembly and Confirmation of Structure","publication_year":2006,"publication_date":"2006-12-08","ids":{"openalex":"https://openalex.org/W2149805101","doi":"https://doi.org/10.1002/anie.200603652","mag":"2149805101","pmid":"https://pubmed.ncbi.nlm.nih.gov/17154210"},"language":"en","primary_location":{"id":"doi:10.1002/anie.200603652","doi":"https://doi.org/10.1002/anie.200603652","is_oa":false,"landing_page_url":"https://doi.org/10.1002/anie.200603652","pdf_url":null,"source":{"id":"https://openalex.org/S67393510","display_name":"Angewandte Chemie International Edition","issn_l":"1433-7851","issn":["1433-7851","1521-3773"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie International Edition","raw_type":"journal-article"},"volume":null,"type":"article","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/A5035782410","display_name":"David Albert Evans","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I136199984","display_name":"Harvard University","ror":"https://ror.org/03vek6s52","country_code":"US","type":"education","lineage":["https://openalex.org/I136199984"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"David\u2005A. Evans","raw_affiliation_strings":["Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA. evans@chemistry.harvard.edu","Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA. evans@chemistry.harvard.edu","institution_ids":["https://openalex.org/I136199984"]},{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,","institution_ids":["https://openalex.org/I136199984"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5075755694","display_name":"Pavel Nagorny","orcid":"https://orcid.org/0000-0002-7043-984X","observed_orcids":["https://orcid.org/0000-0002-7043-984X"]},"institutions":[{"id":"https://openalex.org/I136199984","display_name":"Harvard University","ror":"https://ror.org/03vek6s52","country_code":"US","type":"education","lineage":["https://openalex.org/I136199984"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Pavel Nagorny","raw_affiliation_strings":["Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,","institution_ids":["https://openalex.org/I136199984"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5013583090","display_name":"Kenneth J. McRae","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I136199984","display_name":"Harvard University","ror":"https://ror.org/03vek6s52","country_code":"US","type":"education","lineage":["https://openalex.org/I136199984"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kenneth\u2005J. McRae","raw_affiliation_strings":["Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,","institution_ids":["https://openalex.org/I136199984"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5013636625","display_name":"Louis\u2010Sebastian Sonntag","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I136199984","display_name":"Harvard University","ror":"https://ror.org/03vek6s52","country_code":"US","type":"education","lineage":["https://openalex.org/I136199984"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Louis\u2010Sebastian Sonntag","raw_affiliation_strings":["Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,","institution_ids":["https://openalex.org/I136199984"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5075928380","display_name":"Dominic J. Reynolds","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I136199984","display_name":"Harvard University","ror":"https://ror.org/03vek6s52","country_code":"US","type":"education","lineage":["https://openalex.org/I136199984"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Dominic\u2005J. Reynolds","raw_affiliation_strings":["Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,","institution_ids":["https://openalex.org/I136199984"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5075833885","display_name":"Filisaty Vounatsos","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I136199984","display_name":"Harvard University","ror":"https://ror.org/03vek6s52","country_code":"US","type":"education","lineage":["https://openalex.org/I136199984"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Filisaty Vounatsos","raw_affiliation_strings":["Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138, USA,","institution_ids":["https://openalex.org/I136199984"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I136199984"],"apc_list":{"value":5510,"currency":"USD","value_usd":5510},"apc_paid":null,"fwci":2.0024,"has_fulltext":false,"cited_by_count":30,"citation_normalized_percentile":{"value":0.85301264,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"46","issue":"4","first_page":"545","last_page":"548"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.5971999764442444,"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":0.5971999764442444,"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":0.2856000065803528,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.05000000074505806,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.9509999752044678},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.9549999833106995},{"id":"https://openalex.org/keywords/macrolides","display_name":"macrolides","score":0.8180000185966492},{"id":"https://openalex.org/keywords/fragment-assembly","display_name":"fragment assembly","score":0.7760000228881836},{"id":"https://openalex.org/keywords/structure-confirmation","display_name":"structure confirmation","score":0.5440000295639038}],"concepts":[{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.8328601121902466},{"id":"https://openalex.org/C2776235265","wikidata":"https://www.wikidata.org/wiki/Q18392052","display_name":"Fragment (logic)","level":2,"score":0.711121678352356},{"id":"https://openalex.org/C193557335","wikidata":"https://www.wikidata.org/wiki/Q61424","display_name":"Acylation","level":3,"score":0.6564959287643433},{"id":"https://openalex.org/C61156836","wikidata":"https://www.wikidata.org/wiki/Q494392","display_name":"Aldol reaction","level":3,"score":0.6416609287261963},{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.6073033809661865},{"id":"https://openalex.org/C26517878","wikidata":"https://www.wikidata.org/wiki/Q228039","display_name":"Key (lock)","level":2,"score":0.5376983284950256},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5367485284805298},{"id":"https://openalex.org/C2778152352","wikidata":"https://www.wikidata.org/wiki/Q5165061","display_name":"Content (measure theory)","level":2,"score":0.5074905753135681},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4717058837413788},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.4166228175163269},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.36831116676330566},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2510574758052826},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.18565663695335388},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.12250635027885437},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.11950960755348206},{"id":"https://openalex.org/C38652104","wikidata":"https://www.wikidata.org/wiki/Q3510521","display_name":"Computer security","level":1,"score":0.0},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D003500","descriptor_name":"Cyclization","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":"D015394","descriptor_name":"Molecular Structure","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":false}],"locations_count":2,"locations":[{"id":"doi:10.1002/anie.200603652","doi":"https://doi.org/10.1002/anie.200603652","is_oa":false,"landing_page_url":"https://doi.org/10.1002/anie.200603652","pdf_url":null,"source":{"id":"https://openalex.org/S67393510","display_name":"Angewandte Chemie International Edition","issn_l":"1433-7851","issn":["1433-7851","1521-3773"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Angewandte Chemie International Edition","raw_type":"journal-article"},{"id":"pmid:17154210","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/17154210","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":"Angewandte Chemie (International ed. in English)","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G6684406895","display_name":"ASYMMETRIC SYNTHESIS OF IONOPHORE/MACROLIDE ANTIBIOTICS","funder_award_id":"5r01gm033327-19","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"id":"https://openalex.org/G999064330","display_name":null,"funder_award_id":"GM-33327-19","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"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"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":22,"referenced_works":["https://openalex.org/W1969421659","https://openalex.org/W1974120360","https://openalex.org/W1975632674","https://openalex.org/W1980947232","https://openalex.org/W2005477338","https://openalex.org/W2022412731","https://openalex.org/W2023376243","https://openalex.org/W2057907014","https://openalex.org/W2058499631","https://openalex.org/W2069609532","https://openalex.org/W2072626598","https://openalex.org/W2074632092","https://openalex.org/W2095230314","https://openalex.org/W2107084423","https://openalex.org/W2107842389","https://openalex.org/W2107994731","https://openalex.org/W2178088651","https://openalex.org/W2323943045","https://openalex.org/W2951208272","https://openalex.org/W2951458247","https://openalex.org/W2952998891","https://openalex.org/W4253988104"],"related_works":["https://openalex.org/W2107994731","https://openalex.org/W2125705134","https://openalex.org/W2952920352","https://openalex.org/W2952657149","https://openalex.org/W2952150729","https://openalex.org/W2128444770","https://openalex.org/W2952975519","https://openalex.org/W2949236931","https://openalex.org/W2952257612","https://openalex.org/W2064103754"],"abstract_inverted_index":{"Putting":[0],"the":[1,8,39,46,50],"pieces":[2],"together:":[3],"The":[4,36],"total":[5],"synthesis":[6],"of":[7,38,53],"natural":[9],"macrolide":[10],"oasomycin":[11,54],"A":[12,55],"has":[13],"been":[14],"realized.":[15],"Key":[16],"fragment":[17],"couplings":[18],"include":[19],"an":[20],"anti-Felkin":[21],"selective":[22],"aldol":[23],"addition":[24],"(green),":[25],"Kociensky\u2013Julia":[26],"olefinations":[27],"(red),":[28],"and":[29,45],"competitive":[30],"Weinreb":[31],"amide":[32],"acylation":[33],"reaction":[34],"(blue).":[35],"utility":[37],"4,5-diphenyloxazole":[40],"as":[41],"a":[42],"carboxy":[43],"surrogate":[44],"late-stage":[47],"macrolactonization":[48],"affording":[49],"42-membered":[51],"macrocycle":[52],"are":[56],"also":[57],"described.":[58]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2015,"cited_by_count":4},{"year":2014,"cited_by_count":3},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":3}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}