{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,30]],"date-time":"2026-01-30T02:54:15Z","timestamp":1769741655604,"version":"3.49.0"},"reference-count":95,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2014,11,12]],"date-time":"2014-11-12T00:00:00Z","timestamp":1415750400000},"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":[[2015,1,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>(\u2212)\u2010Lyngbyaloside\u2005B is a 14\u2010membered macrolide glycoside isolated from the marine cyanobacterium <jats:italic>Lyngbya<\/jats:italic> sp. as a cytotoxic substance by Moore and co\u2010workers. The first total synthesis of (\u2212)\u2010lyngbyaloside\u2005B and the reassignment of its stereostructure is described. The synthesis features an Abiko\u2013Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and a macrocyclization involving an acyl ketene intermediate for the construction of the macrocyclic backbone, which contains an acylated tertiary alcohol. The antiproliferative activity of selected compounds against a small panel of human cancer cell lines is also reported.<\/jats:p>","DOI":"10.1002\/anie.201409629","type":"journal-article","created":{"date-parts":[[2014,11,12]],"date-time":"2014-11-12T14:59:33Z","timestamp":1415804373000},"page":"868-873","source":"Crossref","is-referenced-by-count":33,"title":["Total Synthesis, Stereochemical Reassignment, and Biological Evaluation of (\u2212)\u2010Lyngbyaloside\u2005B"],"prefix":"10.1002","volume":"54","author":[{"given":"Haruhiko","family":"Fuwa","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuta","family":"Okuaki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoya","family":"Yamagata","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Makoto","family":"Sasaki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,11,12]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For recent reviews see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.3390\/md10102181"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2010.09.019"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10811-010-9506-x"},{"key":"e_1_2_2_5_2","unstructured":"For examples of marine macrolide glycosides see:"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00056a048"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9621004"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo961302f"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/np020193z"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/np030198b"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo702307t"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900579k"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/np9008128"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/np1000297"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3008622"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/np0202879"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/np1004032"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/np010526c"},{"key":"e_1_2_2_19_2","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","first-page":"712","author":"Gebauer J.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804049"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804049"},{"key":"e_1_2_2_22_2","first-page":"2320","author":"Webb D.","year":"2009","journal-title":"Synlett"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol203064r"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301455p"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol400408w"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300083"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra44354j"},{"key":"e_1_2_2_27_3","first-page":"965","volume":"8","author":"ElMarrouni A.","year":"2013","journal-title":"Nat. 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