{"id":"https://openalex.org/W2117410372","doi":"https://doi.org/10.1080/00397917308065943","title":"A New Route to Cycloheptane-Fused Butyrolactones Based on Cyclopropylcarbinol Solvolysis","display_name":"A New Route to Cycloheptane-Fused Butyrolactones Based on Cyclopropylcarbinol Solvolysis","publication_year":1973,"publication_date":"1973-01-01","ids":{"openalex":"https://openalex.org/W2117410372","doi":"https://doi.org/10.1080/00397917308065943","mag":"2117410372"},"language":"en","primary_location":{"id":"doi:10.1080/00397917308065943","doi":"https://doi.org/10.1080/00397917308065943","is_oa":false,"landing_page_url":"https://doi.org/10.1080/00397917308065943","pdf_url":null,"source":{"id":"https://openalex.org/S114976158","display_name":"Synthetic Communications","issn_l":"0039-7911","issn":["0039-7911","1532-2432"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320547","host_organization_name":"Taylor & Francis","host_organization_lineage":["https://openalex.org/P4310320547","https://openalex.org/P4310320449"],"host_organization_lineage_names":["Taylor & Francis","Informa"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Synthetic Communications","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref"],"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/I111979921","display_name":"Northwestern University","ror":"https://ror.org/000e0be47","country_code":"US","type":"education","lineage":["https://openalex.org/I111979921"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"James A. Marshall","raw_affiliation_strings":["Department of Chemistry, Northwestern University, Evanston, Illinois, 60201, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Northwestern University, Evanston, Illinois, 60201, U.S.A","institution_ids":["https://openalex.org/I111979921"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5044338612","display_name":"F. Norman Tuller","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I111979921","display_name":"Northwestern University","ror":"https://ror.org/000e0be47","country_code":"US","type":"education","lineage":["https://openalex.org/I111979921"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"F. Norman Tuller","raw_affiliation_strings":["Department of Chemistry, Northwestern University, Evanston, Illinois, 60201, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Northwestern University, Evanston, Illinois, 60201, U.S.A","institution_ids":["https://openalex.org/I111979921"]}]},{"author_position":"last","author":{"id":null,"display_name":"Robert Ellison","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I111979921","display_name":"Northwestern University","ror":"https://ror.org/000e0be47","country_code":"US","type":"education","lineage":["https://openalex.org/I111979921"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Robert Ellison","raw_affiliation_strings":["Department of Chemistry, Northwestern University, Evanston, Illinois, 60201, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Northwestern University, Evanston, Illinois, 60201, U.S.A","institution_ids":["https://openalex.org/I111979921"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I111979921"],"apc_list":null,"apc_paid":null,"fwci":1.3127,"has_fulltext":false,"cited_by_count":3,"citation_normalized_percentile":{"value":0.77510422,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":"3","issue":"6","first_page":"465","last_page":"469"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.9307000041007996,"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/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.9307000041007996,"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":0.03759999945759773,"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/T11547","display_name":"Sesquiterpenes and Asteraceae Studies","score":0.010999999940395355,"subfield":{"id":"https://openalex.org/subfields/1306","display_name":"Cancer Research"},"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/hydroazulenes","display_name":"hydroazulenes","score":0.847000002861023},{"id":"https://openalex.org/keywords/gamma-lactones","display_name":"\u03b3-lactones","score":0.6930000185966492},{"id":"https://openalex.org/keywords/delta-lactones","display_name":"\u03b4-lactones","score":0.9990000128746033},{"id":"https://openalex.org/keywords/sesquiterpene-lactones","display_name":"sesquiterpene lactones","score":0.9369999766349792},{"id":"https://openalex.org/keywords/carboxylic-esters","display_name":"carboxylic acid esters","score":0.7860000133514404},{"id":"https://openalex.org/keywords/natural-product-synthesis","display_name":"natural product synthesis","score":0.6669999957084656},{"id":"https://openalex.org/keywords/anticancer-agents","display_name":"anticancer agents","score":0.6259999871253967}],"concepts":[{"id":"https://openalex.org/C2778365270","wikidata":"https://www.wikidata.org/wiki/Q423957","display_name":"Cycloheptane","level":3,"score":0.9393770098686218},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8519729971885681},{"id":"https://openalex.org/C2779293432","wikidata":"https://www.wikidata.org/wiki/Q2628534","display_name":"Solvolysis","level":3,"score":0.7113815546035767},{"id":"https://openalex.org/C2776612806","wikidata":"https://www.wikidata.org/wiki/Q59078","display_name":"Lactone","level":2,"score":0.673715353012085},{"id":"https://openalex.org/C2780107210","wikidata":"https://www.wikidata.org/wiki/Q86495","display_name":"Cyclooctane","level":3,"score":0.5703308582305908},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.569524884223938},{"id":"https://openalex.org/C2777735758","wikidata":"https://www.wikidata.org/wiki/Q817765","display_name":"Path (computing)","level":2,"score":0.4570680856704712},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.38831764459609985},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.25449684262275696},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.12703749537467957},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.12338334321975708},{"id":"https://openalex.org/C94412978","wikidata":"https://www.wikidata.org/wiki/Q103135","display_name":"Hydrolysis","level":2,"score":0.0},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1080/00397917308065943","doi":"https://doi.org/10.1080/00397917308065943","is_oa":false,"landing_page_url":"https://doi.org/10.1080/00397917308065943","pdf_url":null,"source":{"id":"https://openalex.org/S114976158","display_name":"Synthetic Communications","issn_l":"0039-7911","issn":["0039-7911","1532-2432"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320547","host_organization_name":"Taylor & Francis","host_organization_lineage":["https://openalex.org/P4310320547","https://openalex.org/P4310320449"],"host_organization_lineage_names":["Taylor & Francis","Informa"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Synthetic Communications","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":6,"referenced_works":["https://openalex.org/W1989372648","https://openalex.org/W2029600611","https://openalex.org/W2057639901","https://openalex.org/W2312227080","https://openalex.org/W2316345282","https://openalex.org/W2952897486"],"related_works":["https://openalex.org/W1985840284","https://openalex.org/W2951283126","https://openalex.org/W7216594706","https://openalex.org/W2147199680","https://openalex.org/W2137275914","https://openalex.org/W2952393584","https://openalex.org/W2027739140","https://openalex.org/W640725500","https://openalex.org/W2893210583","https://openalex.org/W2079064435"],"abstract_inverted_index":{"A":[0],"sizeable":[1],"number":[2,47],"of":[3,40,48,53,69,79,110,118],"naturally":[4],"occurring":[5],"hydroazulenes":[6],"feature":[7],"a":[8,34,46,80,90,98,103],"\u03b3-lactone-fused":[9],"cycloheptane":[10,55],"ring.1":[11],"These":[12],"substances":[13],"have":[14,44],"attracted":[15],"widespread":[16],"interest":[17],"in":[18,60,76],"recent":[19],"years":[20],"both":[21,114],"as":[22,27],"potential":[23],"chemotherapeutic":[24],"agents2":[25],"and":[26],"challenging":[28],"synthetic":[29,49],"targets.":[30],"In":[31],"connection":[32],"with":[33],"program":[35],"directed":[36],"toward":[37],"the":[38,54,66,77,86,108],"synthesis":[39],"sesquiterpene":[41],"lactones":[42],"we":[43],"examined":[45],"routes":[50],"to":[51,95],"prototypes":[52],"class.":[56],"The":[57],"scheme":[58],"reported":[59],"this":[61],"communication":[62],"is":[63],"based":[64],"on":[65],"expected":[67],"participation":[68],"an":[70],"appropriately":[71],"substituted":[72],"carboxylic":[73],"ester":[74],"function":[75],"solvolysis":[78],"cyclopropylcarbinyl":[81],"system.3":[82],"As":[83],"shown":[84],"below,":[85],"hypothetical":[87],"reaction":[88],"could":[89],"priori":[91],"follow":[92],"two":[93],"pathways":[94,115],"give":[96],"either":[97],"\u03b3-lactone":[99],"(Path":[100,105],"A)":[101],"or":[102],"\u03b4-lactone":[104],"B).":[106],"From":[107],"standpoint":[109],"natural":[111],"products":[112],"synthesis,":[113],"would":[116],"be":[117],"great":[119],"interest.4":[120]},"counts_by_year":[],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2016-06-24T00:00:00"}