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Therefore, research on developing and discovering aminoglycoside antibiotics has recently increased. However, synthetic strategies for controllably positioning the two 1,2\u2010<jats:italic>cis<\/jats:italic>\u2010glycoside moieties on the symmetrical structure of kanamycin have not yet been established. Herein, we report on a novel route for the total synthesis of kanamycins A and B via regio\u2010 and stereoselective introduction of 1,2\u2010<jats:italic>cis<\/jats:italic>\u2010glycosidic linkages as the key step. We successfully synthesized \u03b1(1,6)\u2010linked glycoside using a 1,2\u2010anhydro donor and 2\u2010deoxy\u2010<jats:italic>myo<\/jats:italic>\u2010inositol 1,3,5\u2010orthoformate acceptor in the presence of a boronic acid catalyst via desymmetric boron\u2010mediated aglycon delivery. In addition, we also synthesized \u03b1(1,4)\u2010linked glycoside using its corresponding trichloroacetimidate donor.<\/jats:p>","DOI":"10.1002\/chem.202500685","type":"journal-article","created":{"date-parts":[[2025,4,14]],"date-time":"2025-04-14T22:54:35Z","timestamp":1744671275000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Total Synthesis of Kanamycins"],"prefix":"10.1002","volume":"31","author":[{"given":"Kanae","family":"Hosomi","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3\u201014\u20101 Hiyoshi, Kohoku\u2010ku Yokohama 223\u20138522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Banjo","family":"Imai","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3\u201014\u20101 Hiyoshi, Kohoku\u2010ku Yokohama 223\u20138522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoto","family":"Takemura","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3\u201014\u20101 Hiyoshi, Kohoku\u2010ku Yokohama 223\u20138522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuki","family":"Senoo","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3\u201014\u20101 Hiyoshi, Kohoku\u2010ku Yokohama 223\u20138522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chigusa","family":"Hayashi","sequence":"additional","affiliation":[{"name":"Institute of Microbial Chemistry (BIKAKEN)  3\u201014\u201023 Kamiosaki, Shinagawa\u2010ku Tokyo 141\u20100021 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masayuki","family":"Igarashi","sequence":"additional","affiliation":[{"name":"Institute of Microbial Chemistry (BIKAKEN)  3\u201014\u201023 Kamiosaki, Shinagawa\u2010ku Tokyo 141\u20100021 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3994-9099","authenticated-orcid":false,"given":"Kazunobu","family":"Toshima","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3\u201014\u20101 Hiyoshi, Kohoku\u2010ku Yokohama 223\u20138522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3222-6648","authenticated-orcid":false,"given":"Daisuke","family":"Takahashi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3\u201014\u20101 Hiyoshi, Kohoku\u2010ku Yokohama 223\u20138522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,4,26]]},"reference":[{"key":"e_1_2_6_1_1","first-page":"181","volume":"10","author":"Umezawa H.","year":"1957","journal-title":"J. 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In this case however the overreaction proceeded smoothly and the 1 3 5\u2010tri\u2010mesylated compound was obtained as one of the main products It was therefore decided to proceed further with the synthesis using 36 and 37."},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/b517725a"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202500685","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:44:07Z","timestamp":1760273047000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202500685"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,4,26]]},"references-count":32,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2025,7,8]]}},"alternative-id":["10.1002\/chem.202500685"],"URL":"https:\/\/doi.org\/10.1002\/chem.202500685","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2025,4,26]]},"assertion":[{"value":"2025-02-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-04-14","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-04-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500685"}}