{"id":"https://openalex.org/W1987567713","doi":"https://doi.org/10.1073/pnas.0403887101","title":"Total synthesis of (\u00b1)-halichlorine, (\u00b1)-pinnaic acid, and (\u00b1)-tauropinnaic acid","display_name":"Total synthesis of (\u00b1)-halichlorine, (\u00b1)-pinnaic acid, and (\u00b1)-tauropinnaic acid","publication_year":2004,"publication_date":"2004-08-06","ids":{"openalex":"https://openalex.org/W1987567713","doi":"https://doi.org/10.1073/pnas.0403887101","mag":"1987567713","pmid":"https://pubmed.ncbi.nlm.nih.gov/15299146","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/514438"},"language":"en","primary_location":{"id":"doi:10.1073/pnas.0403887101","doi":"https://doi.org/10.1073/pnas.0403887101","is_oa":false,"landing_page_url":"https://doi.org/10.1073/pnas.0403887101","pdf_url":null,"source":{"id":"https://openalex.org/S125754415","display_name":"Proceedings of the National Academy of Sciences","issn_l":"0027-8424","issn":["0027-8424","1091-6490"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-class-a","anvur-scientific","cwts-core","dongbi-a","doyens","erih-plus","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320052","host_organization_name":"National Academy of Sciences","host_organization_lineage":["https://openalex.org/P4310320052"],"host_organization_lineage_names":["National Academy of Sciences"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Proceedings of the National Academy of Sciences","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"http://europepmc.org/pmc/articles/PMC514438","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5079249232","display_name":"Hamish S. Christie","orcid":"https://orcid.org/0000-0002-8108-6058","observed_orcids":["https://orcid.org/0000-0002-8108-6058"]},"institutions":[{"id":"https://openalex.org/I95457486","display_name":"University of California, Berkeley","ror":"https://ror.org/01an7q238","country_code":"US","type":"education","lineage":["https://openalex.org/I95457486"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Hamish S. Christie","raw_affiliation_strings":["Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720","Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720","institution_ids":["https://openalex.org/I95457486"]},{"raw_affiliation_string":"Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720, USA","institution_ids":["https://openalex.org/I95457486"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5025194991","display_name":"Clayton H. Heathcock","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I123431417","display_name":"Scripps Research Institute","ror":"https://ror.org/02dxx6824","country_code":"US","type":"nonprofit","lineage":["https://openalex.org/I123431417"]},{"id":"https://openalex.org/I95457486","display_name":"University of California, Berkeley","ror":"https://ror.org/01an7q238","country_code":"US","type":"education","lineage":["https://openalex.org/I95457486"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Clayton H. Heathcock","raw_affiliation_strings":["Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720","The Scripps Research Institute, La Jolla, CA,"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720","institution_ids":["https://openalex.org/I95457486"]},{"raw_affiliation_string":"The Scripps Research Institute, La Jolla, CA,","institution_ids":["https://openalex.org/I123431417"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5025194991"],"corresponding_institution_ids":["https://openalex.org/I123431417","https://openalex.org/I95457486"],"apc_list":null,"apc_paid":null,"fwci":3.2201,"has_fulltext":false,"cited_by_count":56,"citation_normalized_percentile":{"value":0.91870409,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"101","issue":"33","first_page":"12079","last_page":"12084"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.7997999787330627,"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":0.7997999787330627,"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":0.07509999722242355,"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":0.06880000233650208,"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/halichlorine","display_name":"halichlorine","score":0.9369999766349792},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.925000011920929},{"id":"https://openalex.org/keywords/marine-natural-products","display_name":"marine natural products","score":0.949999988079071},{"id":"https://openalex.org/keywords/olefin-cross-metathesis","display_name":"olefin cross-metathesis","score":0.9200000166893005},{"id":"https://openalex.org/keywords/hydrogenolysis","display_name":"hydrogenolysis","score":0.722000002861023},{"id":"https://openalex.org/keywords/horner-wadsworth-emmons-reaction","display_name":"Horner-Wadsworth-Emmons reaction","score":0.9380000233650208},{"id":"https://openalex.org/keywords/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.6700000166893005}],"concepts":[{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.8177304267883301},{"id":"https://openalex.org/C2781462491","wikidata":"https://www.wikidata.org/wiki/Q410234","display_name":"Piperidine","level":2,"score":0.7175947427749634},{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.69854736328125},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.694983959197998},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5790113210678101},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.5407145023345947},{"id":"https://openalex.org/C181886296","wikidata":"https://www.wikidata.org/wiki/Q903188","display_name":"Hydrogenolysis","level":3,"score":0.5365327596664429},{"id":"https://openalex.org/C2777811443","wikidata":"https://www.wikidata.org/wiki/Q415233","display_name":"Cyclopentene","level":3,"score":0.48095789551734924},{"id":"https://openalex.org/C51886252","wikidata":"https://www.wikidata.org/wiki/Q4118667","display_name":"Olefin fiber","level":3,"score":0.47511228919029236},{"id":"https://openalex.org/C35753019","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Total synthesis","level":2,"score":0.4638393521308899},{"id":"https://openalex.org/C153914509","wikidata":"https://www.wikidata.org/wiki/Q191090","display_name":"Metathesis","level":4,"score":0.421542763710022},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.31454092264175415},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.307547926902771},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.259393572807312},{"id":"https://openalex.org/C521977710","wikidata":"https://www.wikidata.org/wiki/Q81163","display_name":"Polymer","level":2,"score":0.0},{"id":"https://openalex.org/C44228677","wikidata":"https://www.wikidata.org/wiki/Q181898","display_name":"Polymerization","level":3,"score":0.0}],"mesh":[{"descriptor_ui":"D000470","descriptor_name":"Alkaloids","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000470","descriptor_name":"Alkaloids","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001688","descriptor_name":"Biological Products","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D001688","descriptor_name":"Biological Products","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002625","descriptor_name":"Chemistry, Organic","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D008974","descriptor_name":"Mollusca","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D011161","descriptor_name":"Porifera","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013141","descriptor_name":"Spiro Compounds","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D013141","descriptor_name":"Spiro Compounds","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":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":4,"locations":[{"id":"doi:10.1073/pnas.0403887101","doi":"https://doi.org/10.1073/pnas.0403887101","is_oa":false,"landing_page_url":"https://doi.org/10.1073/pnas.0403887101","pdf_url":null,"source":{"id":"https://openalex.org/S125754415","display_name":"Proceedings of the National Academy of Sciences","issn_l":"0027-8424","issn":["0027-8424","1091-6490"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-class-a","anvur-scientific","cwts-core","dongbi-a","doyens","erih-plus","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320052","host_organization_name":"National Academy of Sciences","host_organization_lineage":["https://openalex.org/P4310320052"],"host_organization_lineage_names":["National Academy of Sciences"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Proceedings of the National Academy of Sciences","raw_type":"journal-article"},{"id":"pmh:oai:europepmc.org:1323190","doi":null,"is_oa":true,"landing_page_url":"http://europepmc.org/pmc/articles/PMC514438","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"","raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:514438","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/514438","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"Proc Natl Acad Sci U S A","raw_type":"Text"},{"id":"pmid:15299146","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15299146","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":"Proceedings of the National Academy of Sciences of the United States of America","raw_type":"Journal Article"}],"best_oa_location":{"id":"pmh:oai:europepmc.org:1323190","doi":null,"is_oa":true,"landing_page_url":"http://europepmc.org/pmc/articles/PMC514438","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"","raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1155370310","display_name":"TOTAL SYNTHESIS OF POLYCYCLIC NATURAL PRODUCTS","funder_award_id":"5r01gm046057-10","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"id":"https://openalex.org/G4401629453","display_name":null,"funder_award_id":"GM 46057","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":45,"referenced_works":["https://openalex.org/W141774154","https://openalex.org/W1968703382","https://openalex.org/W1969335186","https://openalex.org/W1969421659","https://openalex.org/W1978023447","https://openalex.org/W1993800646","https://openalex.org/W2009381692","https://openalex.org/W2011563477","https://openalex.org/W2025424415","https://openalex.org/W2029400187","https://openalex.org/W2030911931","https://openalex.org/W2031748823","https://openalex.org/W2031799240","https://openalex.org/W2033464875","https://openalex.org/W2041769371","https://openalex.org/W2046634017","https://openalex.org/W2047130166","https://openalex.org/W2055684821","https://openalex.org/W2057798603","https://openalex.org/W2066400010","https://openalex.org/W2079846809","https://openalex.org/W2081069004","https://openalex.org/W2083212137","https://openalex.org/W2088927230","https://openalex.org/W2090894403","https://openalex.org/W2136915615","https://openalex.org/W2398917104","https://openalex.org/W2486682533","https://openalex.org/W2949291643","https://openalex.org/W2949757356","https://openalex.org/W2950313224","https://openalex.org/W2950931996","https://openalex.org/W2951186144","https://openalex.org/W2951644475","https://openalex.org/W2951689248","https://openalex.org/W2951934994","https://openalex.org/W2951946676","https://openalex.org/W2951953389","https://openalex.org/W2952106232","https://openalex.org/W2952304164","https://openalex.org/W2952922227","https://openalex.org/W2962894311","https://openalex.org/W4240279172","https://openalex.org/W4242056573","https://openalex.org/W4256601973"],"related_works":["https://openalex.org/W2146569009","https://openalex.org/W2002568463","https://openalex.org/W3131583445","https://openalex.org/W4388766678","https://openalex.org/W85362155","https://openalex.org/W2056498327","https://openalex.org/W2076981637","https://openalex.org/W2091563088","https://openalex.org/W2011563477","https://openalex.org/W2951689248"],"abstract_inverted_index":{"The":[0,14,28,82,102],"related":[1],"marine":[2],"natural":[3,44],"products":[4,45],"halichlorine,":[5],"pinnaic":[6,100],"acid,":[7],"and":[8],"tauropinnaic":[9],"acid":[10],"have":[11],"been":[12],"synthesized.":[13],"described":[15],"route":[16],"provided":[17,70],"access":[18],"to":[19,88,99,116],"all":[20],"three":[21,39],"compounds":[22],"from":[23,33],"a":[24,57,67,112],"common,":[25],"late-stage":[26],"intermediate.":[27],"synthesis":[29],"began":[30],"with":[31],"1-pyrrolidino-1-cyclopentene":[32],"which":[34,92],"an":[35,89],"intermediate":[36],"possessing":[37],"the":[38,43,62,74,94,118],"contiguous":[40],"stereocenters":[41],"of":[42,66],"was":[46,84,97,106],"synthesized":[47],"in":[48],"just":[49],"four":[50],"steps.":[51],"Olefin":[52],"cross":[53],"metathesis":[54],"followed":[55],"by":[56],"hydrogenation/hydrogenolysis":[58],"reaction":[59,96],"stereoselectively":[60],"formed":[61],"piperidine":[63],"ring.":[64],"Use":[65],"beta-lactam":[68,83],"group":[69],"internal":[71],"protection":[72],"for":[73],"highly":[75],"congested":[76],"nitrogen":[77],"atom":[78],"during":[79],"side-chain":[80],"elaboration.":[81],"subsequently":[85],"reduced":[86],"directly":[87],"amino":[90,104],"aldehyde,":[91],"after":[93,111],"Horner-Wadsworth-Emmons":[95],"elaborated":[98],"acid.":[101],"same":[103],"aldehyde":[105],"also":[107],"transformed":[108],"into":[109],"halichlorine":[110],"thiol-mediated":[113],"cyclization":[114],"sequence":[115],"form":[117],"dehydroquinolizidine":[119],"ring":[120],"system.":[121]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":1},{"year":2015,"cited_by_count":3},{"year":2014,"cited_by_count":3},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":4}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
