{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T15:03:04Z","timestamp":1790175784088,"version":"4.1.0"},"reference-count":44,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2013,12,16]],"date-time":"2013-12-16T00:00:00Z","timestamp":1387152000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2014,1,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Two effective tricyclic platforms are reported for the installation of the two constituent sugars,\n                    <jats:sc>L<\/jats:sc>\n                    \u2010vancosamine and\n                    <jats:sc>D<\/jats:sc>\n                    \u2010angolosamine, in a regio\u2010 and stereoselective manner for the synthesis of the pluramycin class of bis\u2010C\u2010glycoside antitumor antibiotics. Two complementary protocols are now available that differ in the order in which the two sugar moieties are installed. Sc(OTf)\n                    <jats:sub>3<\/jats:sub>\n                    was effective as the Lewis acid.\n                  <\/jats:p>","DOI":"10.1002\/anie.201308016","type":"journal-article","created":{"date-parts":[[2013,12,16]],"date-time":"2013-12-16T15:36:51Z","timestamp":1387208211000},"page":"1258-1261","source":"Crossref","is-referenced-by-count":48,"title":["Synthesis of the Pluramycins 1: Two Designed Anthrones as Enabling Platforms for Flexible Bis\u2010C\u2010Glycosylation"],"prefix":"10.1002","volume":"53","author":[{"given":"Kei","family":"Kitamura","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshio","family":"Ando","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takashi","family":"Matsumoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keisuke","family":"Suzuki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,12,16]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","first-page":"75","volume":"9","author":"Maeda K.","year":"1956","journal-title":"J. Antibiot. Ser. A"},{"key":"e_1_2_2_3_2","first-page":"57","volume":"50","author":"S\u00e9quin U.","year":"1986","journal-title":"Prog. Chem. Org. Nat. Prod."},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/b407364a"},{"key":"e_1_2_2_5_2","unstructured":"For reviews on DNA recognition by the pluramycins see:"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00114a007"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar950167a"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527206776359739"},{"key":"e_1_2_2_9_2","unstructured":"For reviews on the synthesis of aryl C\u2010glycosides see:"},{"key":"e_1_2_2_10_2","volume-title":"C\u2010Glycoside Synthesis","author":"Postema M. H. D.","year":"1995"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00405-0"},{"key":"e_1_2_2_12_2","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja107926f"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.05.117"},{"key":"e_1_2_2_15_2","unstructured":"\u00a0"},{"key":"e_1_2_2_16_2","first-page":"399","author":"Yamauchi T.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_2_17_2","first-page":"2654","author":"Shigeta M.","year":"2010","journal-title":"Synlett"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0108640"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0375582"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00103a037"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol7014219"},{"key":"e_1_2_2_22_2","unstructured":"For the O\u2192C\u2010glycoside rearrangement see:"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)88479-8"},{"key":"e_1_2_2_24_2","first-page":"225","author":"Ben A.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_2_25_2","unstructured":"\u00a0"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/1439-7633(20010903)2:9<612::AID-CBIC612>3.0.CO;2-Z"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar8002249"},{"key":"e_1_2_2_28_2","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19850680213"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.38.236"},{"key":"e_1_2_2_31_2","unstructured":"See the following communication in this issue: K. Kitamura Y. Maezawa Y. Ando T. Kusumi T. Matsumoto K. Suzuki Angew. Chem. DOI:;Angew. Chem. Int. Ed. DOI:."},{"key":"e_1_2_2_32_2","unstructured":"For the preparation of tricycles1and2 see the Supporting Information."},{"key":"e_1_2_2_33_2","unstructured":"For the preparation of angolosamine donor3\u2009b see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19790001600"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00071a003"},{"key":"e_1_2_2_36_2","unstructured":"For the preparation of4 see:"},{"key":"e_1_2_2_37_2","first-page":"469","author":"Hsu D.\u2010S.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2013.2"},{"key":"e_1_2_2_39_2","unstructured":"For structure assignment see the Supporting Information."},{"key":"e_1_2_2_40_2","unstructured":"\u00a0"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.57.3607"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9014716"},{"key":"e_1_2_2_43_2","unstructured":"Other reagents (BBr3 BCl3 and CeCl3\/NaI) induced side reactions such as debenzylation and\/or decomposition of the sugar moiety."},{"key":"e_1_2_2_44_2","unstructured":"BF3\u22c5OEt2and [Cp2HfCl2]\/AgOTf also gave mixtures of12 9 and11in varying ratios. No reaction occurred with Y(OTf)3or La(OTf)3."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201308016","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201308016","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T04:25:45Z","timestamp":1697430345000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201308016"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,12,16]]},"references-count":44,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2014,1,27]]}},"alternative-id":["10.1002\/anie.201308016"],"URL":"https:\/\/doi.org\/10.1002\/anie.201308016","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,12,16]]}}}