{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:33:14Z","timestamp":1760783594719,"version":"build-2065373602"},"reference-count":47,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2012,9,27]],"date-time":"2012-09-27T00:00:00Z","timestamp":1348704000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2012,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We have developed two syntheses of vicenistatin and its analogues. Our first\u2010generation strategy included the rapid and sequential assembly of the macrocyclic lactam by using an intermolecular Horner\u2013Wadsworth\u2013Emmons reaction between the C3\u2013C13 fragment and the C1\u2013C2, C14\u2013C19 fragment, followed by an intramolecular Stille coupling reaction. The second\u2010generation strategy utilized a ring\u2010closing metathesis of a hexaene intermediate to generate the desired 20\u2010membered macrolactam. This second\u2010generation strategy made it possible to prepare synthetic analogues of vicenistatin, including the C20\u2010 and\/or C23\u2010demethyl analogues. Evaluation of the cytotoxic effect of these analogues indicated the importance of the fixed conformation of aglycon for determining the biological activity of the vicenistatins.<\/jats:p>","DOI":"10.1002\/asia.201200615","type":"journal-article","created":{"date-parts":[[2012,9,27]],"date-time":"2012-09-27T14:22:36Z","timestamp":1348755756000},"page":"2872-2881","source":"Crossref","is-referenced-by-count":14,"title":["Synthesis and Structure\u2013Activity Relationship of Vicenistatin, a Cytotoxic 20\u2010Membered Macrolactam Glycoside"],"prefix":"10.1002","volume":"7","author":[{"given":"Hayato","family":"Fukuda","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuko","family":"Nishiyama","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shiina","family":"Nakamura","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yutaro","family":"Ohno","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tadashi","family":"Eguchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshiharu","family":"Iwabuchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takeo","family":"Usui","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoki","family":"Kanoh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,9,27]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.45.868"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.50.186"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np049970g"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0700962104"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja710124p"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00267d"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.00744-09"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.46.1076"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00454-7"},{"key":"e_1_2_6_11_2","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.51.688"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/b008878l"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/b111146a"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00455-9"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00792-4"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00820-1"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2003.12.010"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2005.62"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.01.008"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2006.7"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja208927r"},{"key":"e_1_2_6_25_2","unstructured":"\u00a0"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.07.083"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja042848j"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0685250"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.54.211"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/np060555t"},{"key":"e_1_2_6_31_2","first-page":"2589","author":"Fukuda H.","year":"2010","journal-title":"Synlett"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)73285-0"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH01199"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00268a017"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19931050720"},{"key":"e_1_2_6_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199310681"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049883f"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja020091v"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol702982x"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000557"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja994285v"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052939w"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00346a053"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00327a021"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1991.533"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80163-5"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fasia.201200615","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.201200615","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T20:24:16Z","timestamp":1759955056000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.201200615"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,9,27]]},"references-count":47,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2012,12]]}},"alternative-id":["10.1002\/asia.201200615"],"URL":"https:\/\/doi.org\/10.1002\/asia.201200615","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"type":"print","value":"1861-4728"},{"type":"electronic","value":"1861-471X"}],"subject":[],"published":{"date-parts":[[2012,9,27]]}}}