{"id":"https://openalex.org/W2025519571","doi":"https://doi.org/10.1021/jo048459p","title":"Enantiodivergent Formal Synthesis of (+)- and (\u2212)-Cyclophellitol from d -Xylose Based on the Latent Symmetry Concept","display_name":"Enantiodivergent Formal Synthesis of (+)- and (\u2212)-Cyclophellitol from d -Xylose Based on the Latent Symmetry Concept","publication_year":2004,"publication_date":"2004-12-22","ids":{"openalex":"https://openalex.org/W2025519571","doi":"https://doi.org/10.1021/jo048459p","mag":"2025519571","pmid":"https://pubmed.ncbi.nlm.nih.gov/15651835"},"language":"en","primary_location":{"id":"doi:10.1021/jo048459p","doi":"https://doi.org/10.1021/jo048459p","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo048459p","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/A5085405441","display_name":"Artem S. Kireev","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I207123951","display_name":"New Mexico Institute of Mining and Technology","ror":"https://ror.org/005p9kw61","country_code":"US","type":"education","lineage":["https://openalex.org/I207123951"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Artem S. Kireev","raw_affiliation_strings":["Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu","institution_ids":["https://openalex.org/I207123951"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5067103713","display_name":"August T. Breithaupt","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I207123951","display_name":"New Mexico Institute of Mining and Technology","ror":"https://ror.org/005p9kw61","country_code":"US","type":"education","lineage":["https://openalex.org/I207123951"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"August T. Breithaupt","raw_affiliation_strings":["Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu","institution_ids":["https://openalex.org/I207123951"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5070740602","display_name":"William R. Collins","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I207123951","display_name":"New Mexico Institute of Mining and Technology","ror":"https://ror.org/005p9kw61","country_code":"US","type":"education","lineage":["https://openalex.org/I207123951"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"William Collins","raw_affiliation_strings":["Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu","institution_ids":["https://openalex.org/I207123951"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5066264938","display_name":"\u041e\u043b\u0435\u0433 \u041d. \u041d\u0430\u0434\u0435\u0438\u043d","orcid":"https://orcid.org/0000-0003-4461-1674","observed_orcids":["https://orcid.org/0000-0003-4461-1674"]},"institutions":[{"id":"https://openalex.org/I207123951","display_name":"New Mexico Institute of Mining and Technology","ror":"https://ror.org/005p9kw61","country_code":"US","type":"education","lineage":["https://openalex.org/I207123951"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Oleg N. Nadein","raw_affiliation_strings":["Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu","institution_ids":["https://openalex.org/I207123951"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5009000319","display_name":"Alexander Kornienko","orcid":"https://orcid.org/0000-0003-2041-7367","observed_orcids":["https://orcid.org/0000-0003-2041-7367"]},"institutions":[{"id":"https://openalex.org/I207123951","display_name":"New Mexico Institute of Mining and Technology","ror":"https://ror.org/005p9kw61","country_code":"US","type":"education","lineage":["https://openalex.org/I207123951"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Alexander Kornienko","raw_affiliation_strings":["Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801 akornien@nmt.edu","institution_ids":["https://openalex.org/I207123951"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I207123951"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.6837,"has_fulltext":false,"cited_by_count":27,"citation_normalized_percentile":{"value":0.80771672,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":96},"biblio":{"volume":"70","issue":"2","first_page":"742","last_page":"745"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.8842999935150146,"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/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.8842999935150146,"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":0.05810000002384186,"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":0.03830000013113022,"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/cyclophellitol","display_name":"cyclophellitol","score":0.9980000257492065},{"id":"https://openalex.org/keywords/enantiodivergent-synthesis","display_name":"enantiodivergent synthesis","score":0.9649999737739563},{"id":"https://openalex.org/keywords/d-xylose","display_name":"D-xylose","score":0.9409999847412109},{"id":"https://openalex.org/keywords/total-synthesis","display_name":"total synthesis","score":0.6759999990463257},{"id":"https://openalex.org/keywords/biological-evaluation","display_name":"biological evaluation","score":0.335999995470047}],"concepts":[{"id":"https://openalex.org/C2780294150","wikidata":"https://www.wikidata.org/wiki/Q66589603","display_name":"Xylose","level":3,"score":0.8452122211456299},{"id":"https://openalex.org/C486523","wikidata":"https://www.wikidata.org/wiki/Q494483","display_name":"Enantiomer","level":2,"score":0.6576024293899536},{"id":"https://openalex.org/C124668440","wikidata":"https://www.wikidata.org/wiki/Q2305173","display_name":"Chirality (physics)","level":5,"score":0.623731255531311},{"id":"https://openalex.org/C2985598853","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Formal synthesis","level":2,"score":0.5838773250579834},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.495886892080307},{"id":"https://openalex.org/C2781135521","wikidata":"https://www.wikidata.org/wiki/Q8045523","display_name":"Xylose metabolism","level":4,"score":0.48483407497406006},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.43936699628829956},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.43412673473358154},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.29833024740219116},{"id":"https://openalex.org/C52703039","wikidata":"https://www.wikidata.org/wiki/Q5101837","display_name":"Chiral symmetry breaking","level":3,"score":0.22174742817878723},{"id":"https://openalex.org/C204795200","wikidata":"https://www.wikidata.org/wiki/Q903282","display_name":"Symmetry breaking","level":2,"score":0.2182268500328064},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.12731879949569702},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.08858886361122131},{"id":"https://openalex.org/C20621625","wikidata":"https://www.wikidata.org/wiki/Q6961432","display_name":"Nambu\u2013Jona-Lasinio model","level":4,"score":0.0},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0},{"id":"https://openalex.org/C100544194","wikidata":"https://www.wikidata.org/wiki/Q41760","display_name":"Fermentation","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D003511","descriptor_name":"Cyclohexanols","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D003511","descriptor_name":"Cyclohexanols","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":"D014994","descriptor_name":"Xylose","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo048459p","doi":"https://doi.org/10.1021/jo048459p","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo048459p","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:15651835","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15651835","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/G1958911861","display_name":"Enantiodivergent Synthesis of (+) and (-) Pancratistatin","funder_award_id":"R15CA099957","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G6039256589","display_name":null,"funder_award_id":"1-R15-CA099957-01","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":29,"referenced_works":["https://openalex.org/W1538690505","https://openalex.org/W1964203770","https://openalex.org/W1968479888","https://openalex.org/W1973741625","https://openalex.org/W1978115234","https://openalex.org/W1979195097","https://openalex.org/W1994436865","https://openalex.org/W2007407635","https://openalex.org/W2010732799","https://openalex.org/W2013074950","https://openalex.org/W2016261699","https://openalex.org/W2024217355","https://openalex.org/W2025966147","https://openalex.org/W2030236016","https://openalex.org/W2031070923","https://openalex.org/W2079795081","https://openalex.org/W2087891032","https://openalex.org/W2099284213","https://openalex.org/W2106116366","https://openalex.org/W2114037448","https://openalex.org/W2158000362","https://openalex.org/W2161655010","https://openalex.org/W2314122443","https://openalex.org/W2328811441","https://openalex.org/W2950417689","https://openalex.org/W2951869532","https://openalex.org/W2953004176","https://openalex.org/W4240492906","https://openalex.org/W4285719527"],"related_works":["https://openalex.org/W2031674346","https://openalex.org/W2949365520","https://openalex.org/W2114037448","https://openalex.org/W2952800542","https://openalex.org/W1977193713","https://openalex.org/W2059440819","https://openalex.org/W1965587687","https://openalex.org/W2952452033","https://openalex.org/W2169766834","https://openalex.org/W2079739019"],"abstract_inverted_index":{"Formal":[0],"synthesis":[1],"of":[2,13,17,34],"(+)-":[3],"and":[4,31],"(-)-cyclophellitol":[5],"from":[6],"d-xylose":[7],"has":[8],"been":[9],"accomplished":[10],"through":[11],"utilization":[12],"the":[14,21],"latent":[15],"plane":[16],"chirality":[18],"present":[19],"in":[20,37],"starting":[22],"carbohydrate.":[23],"The":[24],"synthetic":[25],"pathway":[26],"is":[27],"suitable":[28],"for":[29],"preparation":[30],"biological":[32],"evaluation":[33],"cyclophellitol":[35],"analogues":[36],"both":[38],"enantiomeric":[39],"series.":[40]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2016,"cited_by_count":2},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}