{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:59:41Z","timestamp":1785286781774,"version":"3.55.0"},"reference-count":57,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T00:00:00Z","timestamp":1785196800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T00:00:00Z","timestamp":1785196800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Substituted piperidines are key synthetic fragments for designing drugs and play a significant role in the pharmaceutical industry. The reported synthetic methods allow access to mono\u2010, di\u2010, and tri\u2010substituted piperidines, but tetra\u2010 and penta\u2010substituted piperidines are scarce in the literature. In this study, exploiting the inherent chirality of iminosugars, we report the synthesis of a levoglucosan mimic in which the endocyclic oxygen of the pyranose ring has been replaced by a\n                    <jats:italic>N<\/jats:italic>\n                    \u2010sulfonyl group. The trans diaxial arrangement of its hydroxyl groups allows navigation on the piperidine ring to iteratively install functional groups at C1, C2, C3, C4, and C6 positions using simple experimental protocols with minimal protecting group manipulation. The broad functional group scope combined with the high regio\u2010 and stereo\u2010selectivity make this approach an appealing process for diversity\u2010oriented synthesis of polysubstituted piperidines, including modified iminosugars. We expect this platform will support drug discovery efforts to accelerate the discovery of therapeutically relevant molecules.\n                  <\/jats:p>","DOI":"10.1002\/chem.71491","type":"journal-article","created":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:25:24Z","timestamp":1785284724000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["<i>N<\/i>\n                    \u2010Sulfonyl Azalevoglucosan: A Versatile Platform for the Synthesis of Polysubstituted Piperidines"],"prefix":"10.1002","author":[{"given":"Dylan","family":"Yorga","sequence":"first","affiliation":[{"name":"Groupe Glycochimie, Equipe OrgaSynth, IC2MP\u2010UMR CNRS 7285 Universit\u00e9 de Poitiers Poitiers cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5351-4908","authenticated-orcid":false,"given":"J\u00e9r\u00f4me","family":"Marrot","sequence":"additional","affiliation":[{"name":"Institut Lavoisier de Versailles, UVSQ, CNRS, UMR 8180 Universit\u00e9 Paris\u2010Saclay  Versailles cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana","family":"Poveda","sequence":"additional","affiliation":[{"name":"ClC bioGUNE Basque Research and Technology Alliance (BRTA)  Derio Spain"},{"name":"Ikerbasque Basque Foundation for Science  Bilbao Spain"},{"name":"Department of Organic &amp; Inorganic Chemistry, Faculty of Science and Technology University of the Basque Country EHU\u2010UPV  Leioa Spain"},{"name":"Centro de Investigacion Biom\u00e9dica En Red De Enfermedades Respiratorias  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2076-2112","authenticated-orcid":false,"given":"Nicolas","family":"Auberger","sequence":"additional","affiliation":[{"name":"Groupe Glycochimie, Equipe OrgaSynth, IC2MP\u2010UMR CNRS 7285 Universit\u00e9 de Poitiers Poitiers cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jes\u00fas","family":"Jim\u00e9nez\u2010Barbero","sequence":"additional","affiliation":[{"name":"ClC bioGUNE Basque Research and Technology Alliance (BRTA)  Derio Spain"},{"name":"Ikerbasque Basque Foundation for Science  Bilbao Spain"},{"name":"Department of Organic &amp; Inorganic Chemistry, Faculty of Science and Technology University of the Basque Country EHU\u2010UPV  Leioa Spain"},{"name":"Centro de Investigacion Biom\u00e9dica En Red De Enfermedades Respiratorias  Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1076-3610","authenticated-orcid":false,"given":"J\u00e9r\u00f4me","family":"D\u00e9sir\u00e9","sequence":"additional","affiliation":[{"name":"Groupe Glycochimie, Equipe OrgaSynth, IC2MP\u2010UMR CNRS 7285 Universit\u00e9 de Poitiers Poitiers cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3209-9282","authenticated-orcid":false,"given":"Yves","family":"Bl\u00e9riot","sequence":"additional","affiliation":[{"name":"Groupe Glycochimie, Equipe OrgaSynth, IC2MP\u2010UMR CNRS 7285 Universit\u00e9 de Poitiers Poitiers cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,28]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.2c00473"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"e_1_2_8_4_1","doi-asserted-by":"crossref","first-page":"e1","DOI":"10.1055\/s-0043-1764218","article-title":"Application of Chiral Piperidine Scaffolds in Drug Design","volume":"5","author":"Chen Q.\u2010S.","year":"2023","journal-title":"Pharmaceutical Fronts"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2md20347b"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms24032937"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010025\u201002008\u20102"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5c00366"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010022\u201000991\u20104"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200901494"},{"key":"e_1_2_8_11_1","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1055\/s-0028-1083325","article-title":"Intermolecular Addition Reactions of N\u2010Acyliminium Ions (Part I)","volume":"2009","author":"Yazici A.","year":"2009","journal-title":"Synthesis"},{"key":"e_1_2_8_12_1","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1055\/s-0028-1083346","article-title":"Intermolecular Addition Reactions of N\u2010Acyliminium Ions (Part II)","volume":"2009","author":"Yazici A.","year":"2009","journal-title":"Synthesis"},{"key":"e_1_2_8_13_1","doi-asserted-by":"crossref","first-page":"3356","DOI":"10.1021\/jacs.8b12689","article-title":"Enantioselective aza\u2010Heck Cyclizations of N\u2010(tosyloxy) Carbamates: Synthesis of Pyrrolidines and Piperidines","volume":"141","author":"Ma X.","year":"2019","journal-title":"Journal of the American Chemical Society"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr078346g"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15070g"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010022\u201000857\u20105"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c13603"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315108"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010023\u201035800\u20100"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c06532"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202313247"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adr9368"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40265\u2010019\u201001090\u20104"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0GC01490G"},{"key":"e_1_2_8_25_1","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/S0065-2318(03)58004-0","article-title":"Chemistry of Anhydrosugars","volume":"58","author":"Cern\u00fd M.","year":"2003","journal-title":"Advances in Carbohydrate Chemistry and Biochemistry"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol035606h"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(01)89351\u20100"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/1522\u20102675(200208)85:8<2235::AID\u2010HLCA2235>3.0.CO;2\u2010I"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010018\u201006901\u2010y"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b08436"},{"key":"e_1_2_8_31_1","first-page":"62","article-title":"Nojirimycin, a new antibiotic. I. Taxonomy and fermentation","volume":"20","author":"Shida N.","year":"1967","journal-title":"Journal of Antibiotics"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(01)86715\u20106"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040\u20104039(95)02237\u20106"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/p29910001991"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200390163"},{"key":"e_1_2_8_36_1","doi-asserted-by":"crossref","first-page":"1707","DOI":"10.1055\/s-2002-33706","article-title":"An Expedient Asymmetric Synthesis of A Calystegine B4 Analogue","volume":"2002","author":"Koulocheri S. D.","year":"2002","journal-title":"Synthesis"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19660991111"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo015639f"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0008\u20106215(98)00287\u20100"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol006907j"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(97)10473\u20107"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr800278z"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c03278"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00469"},{"key":"e_1_2_8_45_1","first-page":"155","volume-title":"Alkaloids: Chemical and Biochemical Perspectives","author":"Schneider M. J.","year":"1996"},{"key":"e_1_2_8_46_1","unstructured":"For Sake of Clarity we Used the Carbohydrate Nomenclature and not the Piperidine Nomenclature."},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1OB06336G"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b00310"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.38.2435"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)84027\u20107"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.11.080"},{"key":"e_1_2_8_52_1","doi-asserted-by":"crossref","DOI":"10.1002\/9780470517437","volume-title":"Iminosugars From Synthesis to Therapeutic Applications","author":"Compain P.","year":"2007"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978\u20100\u201012\u2010381290\u20102.00004\u20105"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.07.011"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0620038"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja037935a"},{"key":"e_1_2_8_57_1","article-title":"Bacterial Peptidoglycan as a Living Polymer","volume":"84","author":"El\u2010Araby A. M.","year":"2025","journal-title":"Chemistry & Biology"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510861"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71491","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71491","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71491","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:25:26Z","timestamp":1785284726000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71491"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,28]]},"references-count":57,"alternative-id":["10.1002\/chem.71491"],"URL":"https:\/\/doi.org\/10.1002\/chem.71491","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,28]]},"assertion":[{"value":"2026-04-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-07","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71491"}}