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Herein we present our full research effort that has led to the synthesis of these molecules. Key aspects of our final strategy include 1)\u2005synthesis of the C1\u2013C9 pyran core (<jats:bold>5<\/jats:bold>) using an AuCl<jats:sub>3<\/jats:sub>\u2010catalysed cyclisation; 2)\u2005formation of C10\u2013C22 vinyl iodide (<jats:bold>55<\/jats:bold>) by sequential bidirectional Stille reactions and 3)\u2005diastereoselective union of these advanced fragments by means of an alkenylzinc addition (d.r.=91:9 at C9). The common callipeltoside aglycon (<jats:bold>4<\/jats:bold>) was completed in a further five steps. Following this, all three sugar fragments were appended to provide the entire callipeltoside family. In addition to this, <jats:sc>D<\/jats:sc>\u2010configured callipeltose\u2005B was synthesised and appended to the callipeltoside aglycon. The <jats:sup>1<\/jats:sup>H\u2005NMR spectrum of this molecule was found to be significantly different to the natural isolate, further supporting our assignment of callipeltoside\u2005B (<jats:bold>2<\/jats:bold>).<\/jats:p>","DOI":"10.1002\/chem.201501877","type":"journal-article","created":{"date-parts":[[2015,7,31]],"date-time":"2015-07-31T06:36:37Z","timestamp":1438324597000},"page":"13261-13277","source":"Crossref","is-referenced-by-count":37,"title":["Callipeltosides A, B and C: Total Syntheses and Structural Confirmation"],"prefix":"10.1002","volume":"21","author":[{"given":"James R.","family":"Frost","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Colin M.","family":"Pearson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas N.","family":"Snaddon","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard A.","family":"Booth","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard M.","family":"Turner","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johan","family":"Gold","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David M.","family":"Shaw","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew J.","family":"Gaunt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Steven V.","family":"Ley","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,7,31]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9621004"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00035-5"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0703978"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo702307t"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/np1000297"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9024929"},{"key":"e_1_2_6_9_2","unstructured":"For deschlorocallipeltoside:"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011424b"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020301)41:5<841::AID-ANIE841>3.0.CO;2-2"},{"key":"e_1_2_6_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020301)114:5<869::AID-ANGE869>3.0.CO;2-G"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0205232"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0155182"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol016416e"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja026235n"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.02.001"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010202)113:3<623::AID-ANGE623>3.0.CO;2-V"},{"key":"e_1_2_6_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010202)40:3<603::AID-ANIE603>3.0.CO;2-O"},{"key":"e_1_2_6_18_4","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010202)113:3<623::AID-ANGE623>3.0.CO;2-V"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0357853"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac200880081773"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0480325"},{"key":"e_1_2_6_23_2","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9906514"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804049"},{"key":"e_1_2_6_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804049"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo101598y"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800086"},{"key":"e_1_2_6_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800086"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204868"},{"key":"e_1_2_6_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204868"},{"key":"e_1_2_6_29_2","unstructured":"For the syntheses of fragments of the callipeltosides see:"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(98)00086-X"},{"key":"e_1_2_6_31_2","first-page":"169","volume":"3","author":"Gurjar M. 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