{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1360285708206791680.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/jo502322m"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/jo502322m"}},{"identifier":{"@type":"PMID","@value":"25517178"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Stereoselective Synthesis of the C1–C29 Part of Amphidinol 3"}],"description":[{"notation":[{"@value":"Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds, respectively. The C21-C29 part was synthesized via successive cross metathesis and oxa-Michael addition sequence to construct the 1,3-diol system at C25 and C27 and Brown asymmetric crotylation to introduce the stereogenic centers at C23 and C24. Coupling of the C1-C20 and C21-C29 parts was achieved by Julia-Kocienski olefination and regio- and stereoselective dihydroxylation of the C20-C21 double bond in the presence of the C4-C5 and C8-C9 double bonds to afford the C1-C29 part of AM3."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380285708206791681","@type":"Researcher","foaf:name":[{"@value":"Takeshi Tsuruda"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry,\rFaculty and Graduate School of Sciences, Kyushu University, 6-10-1\rHakozaki, Higashi-ku, Fukuoka 812-8581, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1030003658870619648","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"70545574"},{"@type":"NRID","@value":"1000070545574"},{"@type":"NRID","@value":"9000257729725"},{"@type":"NRID","@value":"9000014639514"},{"@type":"NRID","@value":"9000404110038"},{"@type":"NRID","@value":"9000396141373"},{"@type":"NRID","@value":"9000263040832"},{"@type":"NRID","@value":"9000399572732"},{"@type":"NRID","@value":"9000006709549"},{"@type":"NRID","@value":"9000350668619"},{"@type":"NRID","@value":"9000383164097"},{"@type":"NRID","@value":"9000006766335"},{"@type":"NRID","@value":"9000397939609"}],"foaf:name":[{"@value":"Makoto Ebine"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry,\rFaculty and Graduate School of Sciences, Kyushu University, 6-10-1\rHakozaki, Higashi-ku, Fukuoka 812-8581, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380285708206791682","@type":"Researcher","foaf:name":[{"@value":"Aya 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Oishi"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry,\rFaculty and Graduate School of Sciences, Kyushu University, 6-10-1\rHakozaki, Higashi-ku, Fukuoka 812-8581, Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00223263"},{"@type":"EISSN","@value":"15206904"}],"prism:publicationName":[{"@value":"The Journal of Organic Chemistry"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2015-01-07","prism:volume":"80","prism:number":"2","prism:startingPage":"859","prism:endingPage":"871"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/jo502322m"}],"createdAt":"2014-12-17","modifiedAt":"2023-04-03","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Molecular%20Structure","dc:title":"Molecular 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