{"id":"https://openalex.org/W2062661971","doi":"https://doi.org/10.1021/jo971448u","title":"Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Syntheses of Indolizidine Alkaloids (\u2212)-205A, (\u2212)-207A, and (\u2212)-235B","display_name":"Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Syntheses of Indolizidine Alkaloids (\u2212)-205A, (\u2212)-207A, and (\u2212)-235B","publication_year":1997,"publication_date":"1997-11-01","ids":{"openalex":"https://openalex.org/W2062661971","doi":"https://doi.org/10.1021/jo971448u","mag":"2062661971","pmid":"https://pubmed.ncbi.nlm.nih.gov/11671929"},"language":"en","primary_location":{"id":"doi:10.1021/jo971448u","doi":"https://doi.org/10.1021/jo971448u","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo971448u","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/A5077943087","display_name":"Daniel L. Comins","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Daniel L. Comins","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5019718332","display_name":"Donald H. LaMunyon","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Donald H. LaMunyon","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5009226541","display_name":"Xinghai Chen","orcid":"https://orcid.org/0009-0000-9672-1969","observed_orcids":["https://orcid.org/0009-0000-9672-1969"]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Xinghai Chen","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I137902535"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":4.4517,"has_fulltext":false,"cited_by_count":94,"citation_normalized_percentile":{"value":0.95566065,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"62","issue":"23","first_page":"8182","last_page":"8187"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","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/T13649","display_name":"Advanced Synthetic Organic Chemistry","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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.009600000455975533,"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/T13971","display_name":"Isoquinoline Alkaloid Synthesis","score":0.0017999999690800905,"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/indolizidine-alkaloids","display_name":"indolizidine alkaloids","score":0.9959999918937683},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.8920000195503235},{"id":"https://openalex.org/keywords/synthetic-intermediates","display_name":"synthetic intermediates","score":0.6729999780654907},{"id":"https://openalex.org/keywords/wittig-olefination","display_name":"Wittig olefination","score":0.8560000061988831},{"id":"https://openalex.org/keywords/chiral-auxiliaries","display_name":"chiral auxiliaries","score":0.44699999690055847},{"id":"https://openalex.org/keywords/vinyl-triflates","display_name":"vinyl triflates","score":0.7070000171661377},{"id":"https://openalex.org/keywords/dess-martin-oxidation","display_name":"Dess-Martin oxidation","score":0.699999988079071},{"id":"https://openalex.org/keywords/amino-aldehydes","display_name":"amino aldehydes","score":0.5230000019073486},{"id":"https://openalex.org/keywords/indolizidines","display_name":"indolizidines","score":0.6600000262260437}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8465961217880249},{"id":"https://openalex.org/C21774173","wikidata":"https://www.wikidata.org/wiki/Q2462024","display_name":"Trifluoromethanesulfonate","level":3,"score":0.631912887096405},{"id":"https://openalex.org/C2779768532","wikidata":"https://www.wikidata.org/wiki/Q33015","display_name":"Indolizidine","level":3,"score":0.5644954442977905},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.5195522904396057},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.473012238740921},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4505192041397095},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.44595247507095337},{"id":"https://openalex.org/C2779485729","wikidata":"https://www.wikidata.org/wiki/Q210385","display_name":"Pyridine","level":2,"score":0.4304601550102234},{"id":"https://openalex.org/C2780071497","wikidata":"https://www.wikidata.org/wiki/Q2746231","display_name":"Chloroformate","level":2,"score":0.4254882037639618},{"id":"https://openalex.org/C2776300020","wikidata":"https://www.wikidata.org/wiki/Q422423","display_name":"Bromide","level":2,"score":0.41680893301963806},{"id":"https://openalex.org/C2776568683","wikidata":"https://www.wikidata.org/wiki/Q23005640","display_name":"Moiety","level":2,"score":0.41123878955841064},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.2437264621257782},{"id":"https://openalex.org/C2777667214","wikidata":"https://www.wikidata.org/wiki/Q70702","display_name":"Alkaloid","level":2,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/jo971448u","doi":"https://doi.org/10.1021/jo971448u","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo971448u","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:11671929","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/11671929","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":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":26,"referenced_works":["https://openalex.org/W1007402265","https://openalex.org/W1968214465","https://openalex.org/W1979840414","https://openalex.org/W1982986536","https://openalex.org/W1986678940","https://openalex.org/W1988354257","https://openalex.org/W1991700756","https://openalex.org/W1995958248","https://openalex.org/W1996892864","https://openalex.org/W1999134339","https://openalex.org/W2001540676","https://openalex.org/W2010834958","https://openalex.org/W2012400723","https://openalex.org/W2016557527","https://openalex.org/W2021481331","https://openalex.org/W2058623521","https://openalex.org/W2069080553","https://openalex.org/W2074859284","https://openalex.org/W2100485097","https://openalex.org/W2501972569","https://openalex.org/W2950039103","https://openalex.org/W2951182261","https://openalex.org/W2951568292","https://openalex.org/W2952275006","https://openalex.org/W2952482483","https://openalex.org/W4285719527"],"related_works":["https://openalex.org/W2951721820","https://openalex.org/W2953300335","https://openalex.org/W2949067254","https://openalex.org/W2046741765","https://openalex.org/W2950766012","https://openalex.org/W2951330727","https://openalex.org/W2117189998","https://openalex.org/W1975234755","https://openalex.org/W2513842210","https://openalex.org/W6990369104"],"abstract_inverted_index":{"Concise":[0],"asymmetric":[1],"syntheses":[2],"of":[3,16,22,37,43,50,62,88,103,110,131,141,146,148,167,173],"indolizidine":[4],"alkaloids":[5,152],"(-)-205A,":[6],"(-)-207A,":[7],"and":[8,34,52,66,75,91,114,117,178,182],"(-)-235B":[9,179],"were":[10],"accomplished":[11,154],"with":[12,73,77,133],"a":[13,40,98,127,138,164],"high":[14],"degree":[15],"stereocontrol":[17],"in":[18,30,58,97,155,180],"eleven":[19],"steps.":[20],"Addition":[21],"4-(1-butenyl)magnesium":[23],"bromide":[24],"to":[25,119],"1-acylpyridinium":[26],"salt":[27],"5,":[28],"prepared":[29],"situ":[31],"from":[32,158],"4-methoxy-3-(triisopropylsilyl)pyridine":[33],"the":[35,63,104,111,134,149],"chloroformate":[36],"(+)-trans-2-(alpha-cumyl)cyclohexanol,":[38],"gave":[39,79,137,175],"91%":[41],"yield":[42,140,166],"diastereomerically":[44],"pure":[45],"dihydropyridone":[46],"6.":[47],"Oxidative":[48],"cleavage":[49,109],"6":[51],"subsequent":[53],"reduction":[54,102],"provided":[55,95,163],"alcohol":[56,122],"7":[57],"81%":[59],"yield.":[60],"Removal":[61],"chiral":[64],"auxilliary":[65],"TIPS":[67],"group":[68],"(NaOMe;":[69],"10%":[70],"HCl),":[71],"N-acylation":[72],"BnOCOCCl,":[74],"treatment":[76],"NCS/Ph(3)P":[78],"chloride":[80],"10.":[81],"Methylation":[82],"at":[83],"C-3,":[84],"copper-mediated":[85],"conjugate":[86],"addition":[87],"4-(benzyloxy)butylmagnesium":[89],"bromide,":[90],"vinyl":[92,105],"triflate":[93,106],"formation":[94],"13":[96],"stereoselective":[99],"fashion.":[100],"Catalytic":[101],"moiety,":[107],"simultaneous":[108],"benzyl":[112],"ether":[113],"Cbz":[115],"groups,":[116],"cyclization":[118],"give":[120],"amino":[121,142],"14":[123,132],"was":[124,153],"effected":[125],"via":[126],"one-pot":[128],"reaction.":[129],"Oxidation":[130],"Dess-Martin":[135],"reagent":[136],"97%":[139],"aldehyde":[143],"4.":[144,159],"Synthesis":[145],"each":[147],"three":[150],"title":[151],"one":[156],"step":[157],"The":[160,169],"Seyferth-Gilbert":[161],"reaction":[162],"41%":[165],"(-)-205A.":[168],"appropriate":[170],"Wittig":[171],"olefination":[172],"4":[174],"indolizidines":[176],"(-)-207A":[177],"70%":[181],"86%":[183],"yield,":[184],"respectively.":[185]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":1},{"year":2020,"cited_by_count":2},{"year":2016,"cited_by_count":4},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":5},{"year":2013,"cited_by_count":3},{"year":2012,"cited_by_count":5}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}