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Our study began with the total synthesis of 13\u2010demethyllyngbyaloside\u2005B, in which an esterification\/ring\u2010closing metathesis (RCM) strategy was successfully used for the efficient construction of the macrocycle. We also established reliable methods for the introduction of the conjugated diene side chain and the <jats:sc>l<\/jats:sc>\u2010rhamnose residue onto the macrocyclic framework. However, the esterification\/RCM strategy proved ineffective for the parent natural product because of the difficulties in acylating the sterically encumbered C\u201013 tertiary alcohol; macrolactionization of a seco\u2010acid was also extensively investigated under various conditions without success. We finally completed the total synthesis of the proposed structure of (\u2212)\u2010lyngbyaloside\u2005B by means of a macrolactonization that involves an acyl ketene as the reactive species. However, the NMR spectroscopic data of our synthetic material did not match those of the authentic material, which indicated that the proposed structure must be re\u2010examined. Inspection of the NMR spectroscopic data of the natural product and molecular mechanics calculations led us to postulate that the configuration of the C\u201010, C\u201011, and C\u201013 stereogenic centers had been incorrectly assigned in the proposed structure. Finally, our revised structure of (\u2212)\u2010lyngbyaloside\u2005B was unambiguously verified through total synthesis.<\/jats:p>","DOI":"10.1002\/chem.201600341","type":"journal-article","created":{"date-parts":[[2016,4,26]],"date-time":"2016-04-26T22:07:55Z","timestamp":1461708475000},"page":"6815-6829","source":"Crossref","is-referenced-by-count":21,"title":["Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (\u2212)\u2010Lyngbyaloside\u2005B"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8619-0631","authenticated-orcid":false,"given":"Haruhiko","family":"Fuwa","sequence":"first","affiliation":[{"name":"Graduate School of Life Sciences Tohoku University  2-1-1 Katahira, Aoba-ku Sendai 980-8577 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoya","family":"Yamagata","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Tohoku University  2-1-1 Katahira, Aoba-ku Sendai 980-8577 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuta","family":"Okuaki","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Tohoku University  2-1-1 Katahira, Aoba-ku Sendai 980-8577 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuya","family":"Ogata","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Tohoku University  2-1-1 Katahira, Aoba-ku Sendai 980-8577 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Asami","family":"Saito","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Tohoku University  2-1-1 Katahira, Aoba-ku Sendai 980-8577 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Makoto","family":"Sasaki","sequence":"additional","affiliation":[{"name":"Graduate School of Life Sciences Tohoku University  2-1-1 Katahira, Aoba-ku Sendai 980-8577 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2016,4,26]]},"reference":[{"key":"e_1_2_5_1_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00129J"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00104D"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00144C"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.3390\/md12084539"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.3390\/md12021066"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3NP70118B"},{"key":"e_1_2_5_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo961302f"},{"key":"e_1_2_5_9_1","unstructured":"\u00a0"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9621004"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00035-5"},{"key":"e_1_2_5_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/np030198b"},{"key":"e_1_2_5_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/np0202879"},{"key":"e_1_2_5_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/np010526c"},{"key":"e_1_2_5_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/np1004032"},{"key":"e_1_2_5_16_1","unstructured":"\u00a0"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804049"},{"key":"e_1_2_5_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804049"},{"key":"e_1_2_5_18_2","first-page":"712","author":"Gebauer J.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_5_19_2","first-page":"2320","author":"Webb D.","year":"2009","journal-title":"Synlett"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol203064r"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301455p"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300083"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra44354j"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.01.109"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201502132"},{"key":"e_1_2_5_25_3","first-page":"965","volume":"8","author":"ElMarrouni A.","year":"2013","journal-title":"Nat. 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