{"id":"https://openalex.org/W2092819374","doi":"https://doi.org/10.1021/jo015936k","title":"Synthesis of Stereopentad Analogues of the C14\u2212C22 Segment of Callystatin A through Additions of Chiral Allenylzinc Reagents to Stereotriads","display_name":"Synthesis of Stereopentad Analogues of the C14\u2212C22 Segment of Callystatin A through Additions of Chiral Allenylzinc Reagents to Stereotriads","publication_year":2001,"publication_date":"2001-10-12","ids":{"openalex":"https://openalex.org/W2092819374","doi":"https://doi.org/10.1021/jo015936k","mag":"2092819374","pmid":"https://pubmed.ncbi.nlm.nih.gov/11701042"},"language":"en","primary_location":{"id":"doi:10.1021/jo015936k","doi":"https://doi.org/10.1021/jo015936k","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo015936k","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","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/A5111555129","display_name":"James Arthur Marshall","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I51556381","display_name":"University of Virginia","ror":"https://ror.org/0153tk833","country_code":"US","type":"education","lineage":["https://openalex.org/I51556381"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"James A. Marshall","raw_affiliation_strings":["Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904","institution_ids":["https://openalex.org/I51556381"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5022205436","display_name":"Gregory M. Schaaf","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I51556381","display_name":"University of Virginia","ror":"https://ror.org/0153tk833","country_code":"US","type":"education","lineage":["https://openalex.org/I51556381"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Gregory M. Schaaf","raw_affiliation_strings":["Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904","institution_ids":["https://openalex.org/I51556381"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I51556381"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.8343,"has_fulltext":false,"cited_by_count":59,"citation_normalized_percentile":{"value":0.9046917,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"66","issue":"23","first_page":"7825","last_page":"7831"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.9204000234603882,"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":0.9204000234603882,"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":0.023800000548362732,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.02160000056028366,"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/anti-addition","display_name":"anti addition","score":0.4090000092983246},{"id":"https://openalex.org/keywords/diastereoselectivity","display_name":"diastereoselectivity","score":0.9789999723434448},{"id":"https://openalex.org/keywords/transition-state-analysis","display_name":"transition state analysis","score":0.4869999885559082},{"id":"https://openalex.org/keywords/steric-control","display_name":"steric control","score":0.6230000257492065},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.5170000195503235}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9754911661148071},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.9022634029388428},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.8163968324661255},{"id":"https://openalex.org/C201194858","wikidata":"https://www.wikidata.org/wiki/Q898238","display_name":"Steric effects","level":2,"score":0.7008579969406128},{"id":"https://openalex.org/C2775855785","wikidata":"https://www.wikidata.org/wiki/Q2270356","display_name":"Metalation","level":2,"score":0.6283198595046997},{"id":"https://openalex.org/C108204754","wikidata":"https://www.wikidata.org/wiki/Q353392","display_name":"Adduct","level":2,"score":0.6115061044692993},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.4528745412826538},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.43209826946258545},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4127078950405121},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.38372090458869934},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.34119096398353577}],"mesh":[{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000970","descriptor_name":"Antineoplastic Agents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D005231","descriptor_name":"Fatty Acids, Unsaturated","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D005231","descriptor_name":"Fatty Acids, Unsaturated","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D011161","descriptor_name":"Porifera","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":"D013329","descriptor_name":"Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015032","descriptor_name":"Zinc","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo015936k","doi":"https://doi.org/10.1021/jo015936k","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo015936k","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:11701042","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/11701042","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":[{"id":"https://openalex.org/G2309534923","display_name":"Synthesis of Tumor Inhibitory Marine Natural Products","funder_award_id":"R01CA090383","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G7844288640","display_name":null,"funder_award_id":"R01 CA 90383-01","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":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":19,"referenced_works":["https://openalex.org/W1967360804","https://openalex.org/W1977121059","https://openalex.org/W2018150265","https://openalex.org/W2032472667","https://openalex.org/W2038050307","https://openalex.org/W2053033341","https://openalex.org/W2058623521","https://openalex.org/W2060031647","https://openalex.org/W2073393896","https://openalex.org/W2102166129","https://openalex.org/W2107084423","https://openalex.org/W2113324659","https://openalex.org/W2949899478","https://openalex.org/W2950019085","https://openalex.org/W2950209999","https://openalex.org/W2950645915","https://openalex.org/W2951457146","https://openalex.org/W2951686514","https://openalex.org/W2952832423"],"related_works":["https://openalex.org/W2952967764","https://openalex.org/W1993481574","https://openalex.org/W2045580185","https://openalex.org/W2952926256","https://openalex.org/W1986743075","https://openalex.org/W2178357880","https://openalex.org/W2949072818","https://openalex.org/W2952832423","https://openalex.org/W2088306722","https://openalex.org/W2047092520"],"abstract_inverted_index":{"The":[0],"addition":[1],"of":[2,13,27,68,76],"(P)-":[3],"and":[4,15,25,31,50,62,78],"(M)-allenylzinc":[5,64],"reagents,":[6],"prepared":[7],"in":[8,74],"situ":[9],"through":[10],"Pd-catalyzed":[11],"metalation":[12],"(R)-":[14],"(S)-3-butyn-2-ol":[16],"mesylates,":[17],"to":[18,37],"diastereomeric":[19],"stereotriad":[20],"aldehydes":[21,41,61],"8,":[22],"13,":[23],"18,":[24],"23":[26],"syn,syn,":[28],"syn,anti,":[29],"anti,anti,":[30],"anti,syn":[32],"stereochemistry":[33],"was":[34,55],"examined.":[35],"Additions":[36],"the":[38,43,58,63],"former":[39],"two":[40,60],"afforded":[42],"four":[44],"anti":[45],"adducts":[46],"with":[47,57],"high":[48],"diastereoselectivity":[49],"negligible":[51],"mismatching.":[52],"Significant":[53],"mismatching":[54],"observed":[56],"latter":[59],"reagent.":[65],"An":[66],"evaluation":[67],"possible":[69],"transition":[70],"states":[71],"is":[72],"presented":[73],"consideration":[75],"steric":[77],"dipolar":[79],"control":[80],"elements.":[81]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2024,"cited_by_count":1},{"year":2022,"cited_by_count":3},{"year":2021,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":4},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":7}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
