{"id":"https://openalex.org/W2017959627","doi":"https://doi.org/10.1021/jo015544d","title":"Synthesis of Enantiomerically and Diastereomerically Pure 2(S)-Amino-6(R)-hydroxy-1,7-heptanedioic Acid Dimethyl Ester Hydrochloride from Cycloheptadiene","display_name":"Synthesis of Enantiomerically and Diastereomerically Pure 2(S)-Amino-6(R)-hydroxy-1,7-heptanedioic Acid Dimethyl Ester Hydrochloride from Cycloheptadiene","publication_year":2001,"publication_date":"2001-06-13","ids":{"openalex":"https://openalex.org/W2017959627","doi":"https://doi.org/10.1021/jo015544d","mag":"2017959627","pmid":"https://pubmed.ncbi.nlm.nih.gov/11442409"},"language":"en","primary_location":{"id":"doi:10.1021/jo015544d","doi":"https://doi.org/10.1021/jo015544d","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo015544d","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/A5077947590","display_name":"Brock T. Shireman","orcid":"https://orcid.org/0000-0003-4062-0274","observed_orcids":["https://orcid.org/0000-0003-4062-0274"]},"institutions":[{"id":"https://openalex.org/I107639228","display_name":"University of Notre Dame","ror":"https://ror.org/00mkhxb43","country_code":"US","type":"education","lineage":["https://openalex.org/I107639228"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Brock T. Shireman","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556","Department of Chemistry and Biochemistry, University of Notre Dame Notre Dame, Indiana 46556 USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556","institution_ids":["https://openalex.org/I107639228"]},{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Notre Dame Notre Dame, Indiana 46556 USA","institution_ids":["https://openalex.org/I107639228"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5091265699","display_name":"Marvin J. Miller","orcid":"https://orcid.org/0000-0002-3704-8214","observed_orcids":["https://orcid.org/0000-0002-3704-8214"]},"institutions":[{"id":"https://openalex.org/I107639228","display_name":"University of Notre Dame","ror":"https://ror.org/00mkhxb43","country_code":"US","type":"education","lineage":["https://openalex.org/I107639228"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Marvin J. Miller","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556","institution_ids":["https://openalex.org/I107639228"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I107639228"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.0723,"has_fulltext":false,"cited_by_count":24,"citation_normalized_percentile":{"value":0.71223716,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":96},"biblio":{"volume":"66","issue":"14","first_page":"4809","last_page":"4813"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.4650999903678894,"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":0.4650999903678894,"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":0.2992999851703644,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.11550000309944153,"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/cycloheptadiene","display_name":"cycloheptadiene","score":0.9120000004768372},{"id":"https://openalex.org/keywords/asymmetric-synthesis","display_name":"asymmetric synthesis","score":0.703000009059906},{"id":"https://openalex.org/keywords/diastereoselective-synthesis","display_name":"diastereoselective synthesis","score":0.9739999771118164},{"id":"https://openalex.org/keywords/transpeptidation","display_name":"transpeptidation","score":0.9919999837875366},{"id":"https://openalex.org/keywords/stereocontrol","display_name":"stereocontrol","score":0.515999972820282}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9257402420043945},{"id":"https://openalex.org/C2776460385","wikidata":"https://www.wikidata.org/wiki/Q420060","display_name":"Hydrochloride","level":2,"score":0.7268997430801392},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.7106263041496277},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.516035795211792},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.440066933631897},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.42471861839294434},{"id":"https://openalex.org/C2781383373","wikidata":"https://www.wikidata.org/wiki/Q4746436","display_name":"Amino esters","level":3,"score":0.413019061088562},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.11493343114852905},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.07744893431663513}],"mesh":[{"descriptor_ui":"D000900","descriptor_name":"Anti-Bacterial Agents","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D002473","descriptor_name":"Cell Wall","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D003960","descriptor_name":"Diaminopimelic Acid","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D003960","descriptor_name":"Diaminopimelic Acid","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D006090","descriptor_name":"Gram-Negative Bacteria","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}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo015544d","doi":"https://doi.org/10.1021/jo015544d","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo015544d","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:11442409","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/11442409","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/G5246208302","display_name":"DRUGS AND DELIVERY SYSTEMS FOR OPPORTUNISTIC INFECTIONS","funder_award_id":"R01AI030988","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"},{"id":"https://openalex.org/G975140997","display_name":null,"funder_award_id":"AI30988","funder_id":"https://openalex.org/F4320337355","funder_display_name":"National Institute of Allergy and Infectious Diseases"}],"funders":[{"id":"https://openalex.org/F4320337355","display_name":"National Institute of Allergy and Infectious Diseases","ror":"https://ror.org/043z4tv69"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":14,"referenced_works":["https://openalex.org/W1973653019","https://openalex.org/W1980975600","https://openalex.org/W1988552097","https://openalex.org/W2017617237","https://openalex.org/W2058147606","https://openalex.org/W2092369303","https://openalex.org/W2094806927","https://openalex.org/W2121521502","https://openalex.org/W2124279942","https://openalex.org/W2128896128","https://openalex.org/W2143893593","https://openalex.org/W2949643490","https://openalex.org/W2952647399","https://openalex.org/W2952972623"],"related_works":["https://openalex.org/W2949359649","https://openalex.org/W2051592795","https://openalex.org/W2026710846","https://openalex.org/W2953101694","https://openalex.org/W2136280971","https://openalex.org/W2950779353","https://openalex.org/W1987428971","https://openalex.org/W2097925489","https://openalex.org/W1978451221","https://openalex.org/W2011774756"],"abstract_inverted_index":{"The":[0],"complete":[1],"carbon":[2],"framework":[3],"of":[4,54,70,78],"enantiomerically":[5],"and":[6,46],"diastereomerically":[7],"pure":[8],"2(S)-amino-6(R)-hydroxy-1,7-heptanedioic":[9],"acid":[10,44,73],"dimethyl":[11],"ester":[12],"hydrochloride":[13],"was":[14],"derived":[15],"from":[16],"cycloheptadiene":[17],"in":[18],"six":[19],"steps":[20],"utilizing":[21],"an":[22],"amino":[23,34,72],"acid-derived":[24],"acylnitroso":[25],"Diels-Alder":[26],"reaction":[27],"as":[28],"the":[29,59,71,76,79],"key":[30],"step.":[31],"This":[32],"versatile":[33],"diester":[35],"has":[36],"been":[37],"previously":[38],"used":[39],"to":[40],"synthesize":[41],"amino-differentiated":[42],"diaminopimelic":[43],"(DAP)":[45],"biologically":[47],"active":[48],"analogues.":[49],"In":[50],"addition,":[51],"after":[52],"formation":[53],"a":[55,67],"novel":[56,68],"aminoxy":[57],"diketopiperazine,":[58],"newly":[60],"formed":[61],"carboxyl":[62],"groups":[63],"were":[64],"differentiated":[65],"by":[66],"transpeptidation":[69],"that":[74],"directed":[75],"stereochemistry":[77],"initial":[80],"cycloaddition.":[81]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2021,"cited_by_count":3},{"year":2017,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
