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However, ANS synthesis has been challenging due to the difficulty in the installation of multi\u2010amino groups. We report herein the development of a concise synthetic route to peracetylated ANSs in seven steps from commercially available monosaccharides. The key to success is the use of the sequential Overman rearrangement, which enables formal simultaneous substitution of four or five hydroxy groups in monosaccharides with amino groups. A variety of ANSs are available through the same reaction sequence starting from different initial monosaccharides by chirality transfer of secondary alcohols. Transformations of the resulting peracetylated ANSs such as glycosylation and deacetylation are also demonstrated. Biological studies reveal that ANS\u2010modified cholesterol show cytotoxicity against human cancer cell lines, whereas each ANS and cholesterol have no cytotoxicity.<\/jats:p>","DOI":"10.1002\/anie.202015141","type":"journal-article","created":{"date-parts":[[2020,11,30]],"date-time":"2020-11-30T19:44:04Z","timestamp":1606765444000},"page":"5193-5198","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Seven\u2010Step Synthesis of All\u2010Nitrogenated Sugar Derivatives Using Sequential Overman Rearrangements"],"prefix":"10.1002","volume":"60","author":[{"given":"Yuya","family":"Okuyama","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mayu","family":"Kidena","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erina","family":"Kato","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sayaka","family":"Kawano","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Koki","family":"Ishii","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kenta","family":"Maie","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4514-6305","authenticated-orcid":false,"given":"Kazuki","family":"Miura","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Siro","family":"Simizu","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5769-3408","authenticated-orcid":false,"given":"Takaaki","family":"Sato","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3074-6914","authenticated-orcid":false,"given":"Noritaka","family":"Chida","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Technology Keio University  3-14-1, Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,1,28]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"For recent selected reviews on aminoglycosides see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.idc.2016.02.011"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2017.117"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsinfecdis.9b00441"},{"key":"e_1_2_2_5_1","unstructured":"For recent selected reviews on iminosugars see:"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)00451-9"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200400823"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.11.117"},{"key":"e_1_2_2_9_1","first-page":"181","volume":"10","author":"Umezawa H.","year":"1957","journal-title":"J. Antibiot."},{"key":"e_1_2_2_10_1","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","unstructured":"R. P.Frohardt T. H.Haskell E.John K. M.Penner US2916485A 1959;"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01045a028"},{"key":"e_1_2_2_13_1","unstructured":"World Health Organization Critically important antimicrobials for human medicine 6th revision 2019."},{"key":"e_1_2_2_14_1","unstructured":"For isolation and biology of nojirimycin see:"},{"key":"e_1_2_2_15_2","first-page":"66","volume":"20","author":"Ishida N.","year":"1967","journal-title":"J. Antibiot. Ser. 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thermal conditions were suitable for the sequential Overman rearrangements. For example PdII-catalyzed rearrangements resulted in no reaction."},{"key":"e_1_2_2_100_1","unstructured":"Although the factors controlling the stereoselectivity at C1 were not elucidated all pAc-ANSs were obtained as a single diastereomer at C1."},{"key":"e_1_2_2_101_1","unstructured":"\u00a0"},{"key":"e_1_2_2_102_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397918508063857"},{"key":"e_1_2_2_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b00475"},{"key":"e_1_2_2_104_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20170408"},{"key":"e_1_2_2_105_1","unstructured":"The formation of oxazolines was indicated by ESI-MS spectra of the crude compound. 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