{"id":"https://openalex.org/W2951414944","doi":"https://doi.org/10.1021/jo9919862","title":"Synthesis of Cryptophycin 52 Using the Sharpless Asymmetric Dihydroxylation: Diol to Epoxide Transformation Optimized for a Base-Sensitive Substrate","display_name":"Synthesis of Cryptophycin 52 Using the Sharpless Asymmetric Dihydroxylation: Diol to Epoxide Transformation Optimized for a Base-Sensitive Substrate","publication_year":2000,"publication_date":"2000-04-12","ids":{"openalex":"https://openalex.org/W2951414944","doi":"https://doi.org/10.1021/jo9919862","mag":"2951414944","pmid":"https://pubmed.ncbi.nlm.nih.gov/10814209"},"language":"en","primary_location":{"id":"doi:10.1021/jo9919862","doi":"https://doi.org/10.1021/jo9919862","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo9919862","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":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5059802734","display_name":"Jian Liang","orcid":"https://orcid.org/0009-0002-7940-6590","observed_orcids":["https://orcid.org/0009-0002-7940-6590"]},"institutions":[{"id":"https://openalex.org/I117965899","display_name":"University of Hawai\u02bbi at M\u0101noa","ror":"https://ror.org/01wspgy28","country_code":"US","type":"education","lineage":["https://openalex.org/I117965899"]},{"id":"https://openalex.org/I1331384533","display_name":"University of Hawaii System","ror":"https://ror.org/03tzaeb71","country_code":"US","type":"education","lineage":["https://openalex.org/I1331384533"]},{"id":"https://openalex.org/I168537998","display_name":"Eli Lilly (United States)","ror":"https://ror.org/01qat3289","country_code":"US","type":"company","lineage":["https://openalex.org/I168537998"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jian Liang","raw_affiliation_strings":["Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285","institution_ids":["https://openalex.org/I117965899","https://openalex.org/I1331384533","https://openalex.org/I168537998"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5031073315","display_name":"Eric D. Moher","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I117965899","display_name":"University of Hawai\u02bbi at M\u0101noa","ror":"https://ror.org/01wspgy28","country_code":"US","type":"education","lineage":["https://openalex.org/I117965899"]},{"id":"https://openalex.org/I1331384533","display_name":"University of Hawaii System","ror":"https://ror.org/03tzaeb71","country_code":"US","type":"education","lineage":["https://openalex.org/I1331384533"]},{"id":"https://openalex.org/I168537998","display_name":"Eli Lilly (United States)","ror":"https://ror.org/01qat3289","country_code":"US","type":"company","lineage":["https://openalex.org/I168537998"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Eric D. Moher","raw_affiliation_strings":["Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285","institution_ids":["https://openalex.org/I117965899","https://openalex.org/I1331384533","https://openalex.org/I168537998"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5107595054","display_name":"Richard E. Moore","orcid":"https://orcid.org/0000-0002-5328-9018","observed_orcids":["https://orcid.org/0000-0002-5328-9018"]},"institutions":[{"id":"https://openalex.org/I117965899","display_name":"University of Hawai\u02bbi at M\u0101noa","ror":"https://ror.org/01wspgy28","country_code":"US","type":"education","lineage":["https://openalex.org/I117965899"]},{"id":"https://openalex.org/I1331384533","display_name":"University of Hawaii System","ror":"https://ror.org/03tzaeb71","country_code":"US","type":"education","lineage":["https://openalex.org/I1331384533"]},{"id":"https://openalex.org/I168537998","display_name":"Eli Lilly (United States)","ror":"https://ror.org/01qat3289","country_code":"US","type":"company","lineage":["https://openalex.org/I168537998"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Richard E. Moore","raw_affiliation_strings":["Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285","institution_ids":["https://openalex.org/I117965899","https://openalex.org/I1331384533","https://openalex.org/I168537998"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5038817888","display_name":"David W. Hoard","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I117965899","display_name":"University of Hawai\u02bbi at M\u0101noa","ror":"https://ror.org/01wspgy28","country_code":"US","type":"education","lineage":["https://openalex.org/I117965899"]},{"id":"https://openalex.org/I1331384533","display_name":"University of Hawaii System","ror":"https://ror.org/03tzaeb71","country_code":"US","type":"education","lineage":["https://openalex.org/I1331384533"]},{"id":"https://openalex.org/I168537998","display_name":"Eli Lilly (United States)","ror":"https://ror.org/01qat3289","country_code":"US","type":"company","lineage":["https://openalex.org/I168537998"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"David W. Hoard","raw_affiliation_strings":["Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, and Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285","institution_ids":["https://openalex.org/I117965899","https://openalex.org/I1331384533","https://openalex.org/I168537998"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":5.502,"has_fulltext":false,"cited_by_count":51,"citation_normalized_percentile":{"value":0.97129547,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"65","issue":"10","first_page":"3143","last_page":"3147"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.7480000257492065,"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":0.7480000257492065,"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":0.09839999675750732,"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":0.08829999715089798,"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/sharpless-asymmetric-dihydroxylation","display_name":"Sharpless asymmetric dihydroxylation","score":0.8999999761581421},{"id":"https://openalex.org/keywords/epoxide-synthesis","display_name":"epoxide synthesis","score":0.6610000133514404},{"id":"https://openalex.org/keywords/diastereoselectivity","display_name":"diastereoselectivity","score":0.8379999995231628},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.6869999766349792},{"id":"https://openalex.org/keywords/natural-product-synthesis","display_name":"natural product synthesis","score":0.4560000002384186},{"id":"https://openalex.org/keywords/epoxidation","display_name":"epoxidation","score":0.5040000081062317}],"concepts":[{"id":"https://openalex.org/C2776920199","wikidata":"https://www.wikidata.org/wiki/Q408028","display_name":"Epoxide","level":3,"score":0.885589599609375},{"id":"https://openalex.org/C2777672777","wikidata":"https://www.wikidata.org/wiki/Q19903952","display_name":"Dihydroxylation","level":4,"score":0.8605034351348877},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.823971688747406},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.6626455187797546},{"id":"https://openalex.org/C2776626252","wikidata":"https://www.wikidata.org/wiki/Q752651","display_name":"Sharpless asymmetric dihydroxylation","level":4,"score":0.656734824180603},{"id":"https://openalex.org/C2779515768","wikidata":"https://www.wikidata.org/wiki/Q421916","display_name":"Diol","level":2,"score":0.6486128568649292},{"id":"https://openalex.org/C2776568683","wikidata":"https://www.wikidata.org/wiki/Q23005640","display_name":"Moiety","level":2,"score":0.6370589733123779},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.6154934763908386},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.5234733819961548},{"id":"https://openalex.org/C2775890271","wikidata":"https://www.wikidata.org/wiki/Q902026","display_name":"Sharpless epoxidation","level":4,"score":0.46562737226486206},{"id":"https://openalex.org/C2781109383","wikidata":"https://www.wikidata.org/wiki/Q898497","display_name":"Hydroxylation","level":3,"score":0.4233776926994324},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3436497151851654},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.2824367880821228},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0644056499004364},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D002851","descriptor_name":"Chromatography, High Pressure Liquid","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D007769","descriptor_name":"Lactams","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D007769","descriptor_name":"Lactams","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D007783","descriptor_name":"Lactones","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D007783","descriptor_name":"Lactones","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D047630","descriptor_name":"Depsipeptides","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo9919862","doi":"https://doi.org/10.1021/jo9919862","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo9919862","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:10814209","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/10814209","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":36,"referenced_works":["https://openalex.org/W1969014625","https://openalex.org/W1970041255","https://openalex.org/W1972295258","https://openalex.org/W1997846715","https://openalex.org/W1998512233","https://openalex.org/W2000524564","https://openalex.org/W2007396354","https://openalex.org/W2008670873","https://openalex.org/W2012116265","https://openalex.org/W2017372573","https://openalex.org/W2019701027","https://openalex.org/W2024167050","https://openalex.org/W2035266859","https://openalex.org/W2035966343","https://openalex.org/W2045677120","https://openalex.org/W2046818662","https://openalex.org/W2055509249","https://openalex.org/W2060175821","https://openalex.org/W2060487027","https://openalex.org/W2065189412","https://openalex.org/W2067144186","https://openalex.org/W2069348304","https://openalex.org/W2071757789","https://openalex.org/W2077853182","https://openalex.org/W2080788358","https://openalex.org/W2122975129","https://openalex.org/W2125537420","https://openalex.org/W2950218522","https://openalex.org/W2950481949","https://openalex.org/W2950532880","https://openalex.org/W2950806931","https://openalex.org/W2951338143","https://openalex.org/W2951978393","https://openalex.org/W2952735927","https://openalex.org/W2952911174","https://openalex.org/W2953011238"],"related_works":["https://openalex.org/W1974551411","https://openalex.org/W2094678052","https://openalex.org/W2078129344","https://openalex.org/W2949898762","https://openalex.org/W2951120737","https://openalex.org/W2950923121","https://openalex.org/W2004654587","https://openalex.org/W2089152335","https://openalex.org/W788635621","https://openalex.org/W7008881806"],"abstract_inverted_index":{"A":[0],"synthesis":[1],"of":[2,23,33,45,56,80],"cryptophycin":[3,46],"52":[4],"(2)":[5],"is":[6,37,65],"reported":[7],"using":[8],"a":[9],"Sharpless":[10],"asymmetric":[11],"dihydroxylation":[12],"(AD)":[13],"strategy":[14],"to":[15,40,61,72],"install":[16],"the":[17,24,35,41,57,62,78],"epoxide":[18,36,64],"moiety.":[19],"The":[20,67],"high":[21,75],"stereoselectivity":[22],"AD":[25,59],"reaction":[26],"that":[27],"allows":[28],"for":[29,54],"an":[30],"efficient":[31],"means":[32],"preparing":[34],"in":[38,74,77],"contrast":[39],"standard":[42],"direct":[43],"epoxidation":[44],"substrates,":[47],"which":[48],"proceeds":[49],"with":[50],"poor":[51],"diastereoselectivity.":[52],"Methodology":[53],"conversion":[55],"diol":[58],"product":[60],"requisite":[63],"disclosed.":[66],"transformation":[68],"has":[69],"been":[70],"optimized":[71],"proceed":[73],"yield":[76],"presence":[79],"base":[81],"sensitive":[82],"functionality.":[83]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2022,"cited_by_count":3},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2017,"cited_by_count":3},{"year":2016,"cited_by_count":1},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2019-06-27T00:00:00"}
