{"id":"https://openalex.org/W7165933901","doi":"https://doi.org/10.1080/14786419.2026.2685261","title":"Diastereoselective synthesis and structural elucidation of dammarane hollongdione pyrazolines","display_name":"Diastereoselective synthesis and structural elucidation of dammarane hollongdione pyrazolines","publication_year":2026,"publication_date":"2026-06-25","ids":{"openalex":"https://openalex.org/W7165933901","doi":"https://doi.org/10.1080/14786419.2026.2685261","pmid":"https://pubmed.ncbi.nlm.nih.gov/42347735"},"language":"en","primary_location":{"id":"doi:10.1080/14786419.2026.2685261","doi":"https://doi.org/10.1080/14786419.2026.2685261","is_oa":false,"landing_page_url":"https://doi.org/10.1080/14786419.2026.2685261","pdf_url":null,"source":{"id":"https://openalex.org/S205999849","display_name":"Natural Product Research","issn_l":"1478-6419","issn":["1478-6419","1478-6427"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","jufo-1","ki-jl-1","medline","norway-1","poland-70","russia-white-list-1"],"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":"Natural Product Research","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/A5028850829","display_name":"Zarema I. Galimova","orcid":"https://orcid.org/0009-0004-8351-4070","observed_orcids":["https://orcid.org/0009-0004-8351-4070"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210104186","display_name":"Ufa Institute of Chemistry","ror":"https://ror.org/01k8ec266","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210104186","https://openalex.org/I4210145551"]}],"countries":["RU"],"is_corresponding":false,"raw_author_name":"Zarema Galimova","raw_affiliation_strings":["Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry"],"raw_orcid":"https://orcid.org/0009-0004-8351-4070","affiliations":[{"raw_affiliation_string":"Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210104186"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5008139135","display_name":"Irina E. Smirnova","orcid":"https://orcid.org/0000-0001-7176-505X","observed_orcids":["https://orcid.org/0000-0001-7176-505X"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210104186","display_name":"Ufa Institute of Chemistry","ror":"https://ror.org/01k8ec266","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210104186","https://openalex.org/I4210145551"]}],"countries":["RU"],"is_corresponding":true,"raw_author_name":"Irina Smirnova","raw_affiliation_strings":["Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry"],"raw_orcid":"https://orcid.org/0000-0001-7176-505X","affiliations":[{"raw_affiliation_string":"Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210104186"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5008662669","display_name":"Alexander I. Poptsov","orcid":"https://orcid.org/0000-0002-5193-7931","observed_orcids":["https://orcid.org/0000-0002-5193-7931"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210104186","display_name":"Ufa Institute of Chemistry","ror":"https://ror.org/01k8ec266","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210104186","https://openalex.org/I4210145551"]}],"countries":["RU"],"is_corresponding":false,"raw_author_name":"Alexander Poptsov","raw_affiliation_strings":["Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry"],"raw_orcid":"https://orcid.org/0000-0002-5193-7931","affiliations":[{"raw_affiliation_string":"Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210104186"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110768836","display_name":"Svetlana F. Petrova","orcid":"https://orcid.org/0000-0003-1406-0293","observed_orcids":["https://orcid.org/0000-0003-1406-0293"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210104186","display_name":"Ufa Institute of Chemistry","ror":"https://ror.org/01k8ec266","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210104186","https://openalex.org/I4210145551"]}],"countries":["RU"],"is_corresponding":false,"raw_author_name":"Svetlana Petrova","raw_affiliation_strings":["Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry"],"raw_orcid":"https://orcid.org/0000-0003-1406-0293","affiliations":[{"raw_affiliation_string":"Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210104186"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5058390964","display_name":"Oxana B. Kazakova","orcid":"https://orcid.org/0000-0002-5606-1588","observed_orcids":["https://orcid.org/0000-0002-5606-1588","https://orcid.org/0000-0002-8243-9636"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210104186","display_name":"Ufa Institute of Chemistry","ror":"https://ror.org/01k8ec266","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210104186","https://openalex.org/I4210145551"]}],"countries":["RU"],"is_corresponding":false,"raw_author_name":"Oxana Kazakova","raw_affiliation_strings":["Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry"],"raw_orcid":"https://orcid.org/0000-0002-5606-1588","affiliations":[{"raw_affiliation_string":"Ufa Federal Research Center, Russian Academy of Sciences, Ufa Institute of Chemistry","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210104186"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5008139135"],"corresponding_institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210104186"],"apc_list":null,"apc_paid":null,"fwci":0.0,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":{"value":0.39591368,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":null,"issue":null,"first_page":"1","last_page":"7"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11385","display_name":"Natural product bioactivities and synthesis","score":0.6699000000953674,"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"}},"topics":[{"id":"https://openalex.org/T11385","display_name":"Natural product bioactivities and synthesis","score":0.6699000000953674,"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"}},{"id":"https://openalex.org/T13221","display_name":"Biological Activity of Diterpenoids and Biflavonoids","score":0.05990000069141388,"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"}},{"id":"https://openalex.org/T12685","display_name":"Phytochemical compounds biological activities","score":0.02449999935925007,"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/diastereoselective-synthesis","display_name":"diastereoselective synthesis","score":0.9419999718666077},{"id":"https://openalex.org/keywords/dipterocarpus-alatus","display_name":"Dipterocarpus alatus","score":0.9020000100135803},{"id":"https://openalex.org/keywords/ozonolysis","display_name":"ozonolysis","score":0.9139999747276306},{"id":"https://openalex.org/keywords/claisen-schmidt-condensation","display_name":"Claisen-Schmidt condensation","score":0.9869999885559082},{"id":"https://openalex.org/keywords/hydrazides","display_name":"hydrazides","score":0.8109999895095825},{"id":"https://openalex.org/keywords/diastereomer-separation","display_name":"diastereomer separation","score":0.734000027179718},{"id":"https://openalex.org/keywords/natural-product-structure-elucidation","display_name":"natural product structure elucidation","score":0.6449999809265137},{"id":"https://openalex.org/keywords/triterpenoids","display_name":"triterpenoids","score":0.47999998927116394}],"concepts":[{"id":"https://openalex.org/C2779754220","wikidata":"https://www.wikidata.org/wiki/Q5212679","display_name":"Dammarane","level":4,"score":0.9041000008583069},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.863099992275238},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5730999708175659},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.5539000034332275},{"id":"https://openalex.org/C2780744904","wikidata":"https://www.wikidata.org/wiki/Q7263415","display_name":"Pyrazoline","level":2,"score":0.5285999774932861},{"id":"https://openalex.org/C2779173278","wikidata":"https://www.wikidata.org/wiki/Q898508","display_name":"Ozonolysis","level":2,"score":0.5008000135421753},{"id":"https://openalex.org/C68381374","wikidata":"https://www.wikidata.org/wiki/Q258652","display_name":"Double bond","level":2,"score":0.47839999198913574},{"id":"https://openalex.org/C111771559","wikidata":"https://www.wikidata.org/wiki/Q66295","display_name":"Derivative (finance)","level":2,"score":0.4422000050544739},{"id":"https://openalex.org/C2778032409","wikidata":"https://www.wikidata.org/wiki/Q420409","display_name":"Ionone","level":2,"score":0.3935000002384186},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3630000054836273},{"id":"https://openalex.org/C114373084","wikidata":"https://www.wikidata.org/wiki/Q273499","display_name":"Chemical synthesis","level":3,"score":0.3319000005722046},{"id":"https://openalex.org/C200093464","wikidata":"https://www.wikidata.org/wiki/Q166583","display_name":"Condensation","level":2,"score":0.32420000433921814},{"id":"https://openalex.org/C175528265","wikidata":"https://www.wikidata.org/wiki/Q500256","display_name":"Chemical structure","level":2,"score":0.3172999918460846},{"id":"https://openalex.org/C54516573","wikidata":"https://www.wikidata.org/wiki/Q2294","display_name":"Proton","level":2,"score":0.2948000133037567},{"id":"https://openalex.org/C2779746879","wikidata":"https://www.wikidata.org/wiki/Q3010548","display_name":"Enone","level":2,"score":0.28450000286102295},{"id":"https://openalex.org/C202235601","wikidata":"https://www.wikidata.org/wiki/Q7361732","display_name":"Structural isomer","level":2,"score":0.2815000116825104},{"id":"https://openalex.org/C2988005100","wikidata":"https://www.wikidata.org/wiki/Q1979695","display_name":"Proton magnetic resonance","level":2,"score":0.2777999937534332},{"id":"https://openalex.org/C24961977","wikidata":"https://www.wikidata.org/wiki/Q225972","display_name":"Bicyclic molecule","level":2,"score":0.27379998564720154},{"id":"https://openalex.org/C2779396153","wikidata":"https://www.wikidata.org/wiki/Q901227","display_name":"Natural product","level":2,"score":0.27059999108314514},{"id":"https://openalex.org/C207245611","wikidata":"https://www.wikidata.org/wiki/Q910058","display_name":"Condensation reaction","level":3,"score":0.2581999897956848},{"id":"https://openalex.org/C2776300020","wikidata":"https://www.wikidata.org/wiki/Q422423","display_name":"Bromide","level":2,"score":0.25760000944137573},{"id":"https://openalex.org/C103319777","wikidata":"https://www.wikidata.org/wiki/Q1979695","display_name":"Proton NMR","level":2,"score":0.25060001015663147},{"id":"https://openalex.org/C2776920199","wikidata":"https://www.wikidata.org/wiki/Q408028","display_name":"Epoxide","level":3,"score":0.2500999867916107}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1080/14786419.2026.2685261","doi":"https://doi.org/10.1080/14786419.2026.2685261","is_oa":false,"landing_page_url":"https://doi.org/10.1080/14786419.2026.2685261","pdf_url":null,"source":{"id":"https://openalex.org/S205999849","display_name":"Natural Product Research","issn_l":"1478-6419","issn":["1478-6419","1478-6427"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","jufo-1","ki-jl-1","medline","norway-1","poland-70","russia-white-list-1"],"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":"Natural Product Research","raw_type":"journal-article"},{"id":"pmid:42347735","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/42347735","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":"Natural product research","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"sustainable_development_goals_aurora":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":27,"referenced_works":["https://openalex.org/W1982264579","https://openalex.org/W1988983526","https://openalex.org/W1989703419","https://openalex.org/W2010387510","https://openalex.org/W2037440931","https://openalex.org/W2040935847","https://openalex.org/W2076113199","https://openalex.org/W2087722410","https://openalex.org/W2089475777","https://openalex.org/W2089775130","https://openalex.org/W2119438677","https://openalex.org/W2142343268","https://openalex.org/W2414880242","https://openalex.org/W3046865650","https://openalex.org/W3101977820","https://openalex.org/W3162819754","https://openalex.org/W3186451026","https://openalex.org/W4200008950","https://openalex.org/W4246139334","https://openalex.org/W4285491493","https://openalex.org/W4311459057","https://openalex.org/W4312963764","https://openalex.org/W4387062624","https://openalex.org/W4388912974","https://openalex.org/W4392955082","https://openalex.org/W4401173940","https://openalex.org/W4409148986"],"related_works":[],"abstract_inverted_index":{"An":[0],"efficient":[1],"multistep":[2],"synthesis":[3],"of":[4,22,24,28,56,66,78,106],"novel":[5],"substituted":[6],"pyrazoline":[7],"derivatives":[8],"linked":[9],"to":[10,40,44],"a":[11,41,46,49,76,83,122,131],"dammarane":[12],"scaffold":[13],"was":[14,37,60,102],"developed":[15],"for":[16,126,135],"the":[17,25,54,57,67,98,103,107,119,127,136],"first":[18],"time.":[19],"Initially,":[20],"ozonolysis":[21],"one":[23],"main":[26],"metabolites":[27],"Dipterocarpus":[29],"alatus":[30],"-":[31],"3\u03b2-hydroxy-dipterocarpol":[32],"afforded":[33],"natural":[34],"3\u03b2-hydroxy-hollongdione,":[35],"which":[36,86],"subsequently":[38],"subjected":[39],"Claisen\u2013Schmidt":[42],"condensation":[43],"furnish":[45],"derivative":[47],"bearing":[48],"[3-(pyridin-2-yl)-prop-2-en-1-one]-fragment":[50],"at":[51,111],"C17":[52],"and":[53,80,100,114,130],"E-configuration":[55],"double":[58],"bond":[59],"confirmed":[61],"by":[62,90],"spectral":[63],"analysis.":[64],"Cycloaddition":[65],"enone":[68],"intermediates":[69],"with":[70],"formyl":[71],"or":[72],"acetyl":[73],"hydrazides":[74],"produced":[75],"mixture":[77],"S-":[79],"R-diastereomers":[81],"in":[82],"55:45":[84],"ratio,":[85],"were":[87],"successfully":[88],"separated":[89],"HPLC.":[91],"The":[92],"most":[93],"prominent":[94],"distinguishing":[95],"feature":[96],"between":[97],"R-":[99],"S-isomers":[101],"chemical":[104],"shift":[105,134],"H-17":[108],"proton,":[109],"appearing":[110],"\u03b4":[112,115],"2.62":[113],"2.67,":[116],"respectively.":[117],"Additionally,":[118],"R-isomer":[120],"exhibited":[121],"more":[123],"downfield":[124],"resonance":[125],"Ha-3\u2032":[128],"proton":[129],"relatively":[132],"upfield":[133],"Hb-3\u2032":[137],"proton.":[138]},"counts_by_year":[],"updated_date":"2026-10-13T10:08:12.033832","created_date":"2026-06-26T00:00:00"}