{"@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/1360004239431088896.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.3389/fchem.2014.00116"}},{"identifier":{"@type":"PMID","@value":"25629027"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Concise synthesis of the A/BCD-ring fragment of gambieric acid A"}],"description":[{"notation":[{"@value":"Gambieric acid A (GAA) and its congeners belong to the family of marine polycyclic ether natural products. Their highly complex molecular architecture and unique biological activities have been of intense interest within the synthetic community. We have previously reported the first total synthesis, stereochemical reassignment, and preliminary structure-activity relationships of GAA. Here we disclose a concise synthesis of the A/BCD-ring fragment of GAA. The synthesis started from our previously reported synthetic intermediate that represents the A/B-ring. The C-ring was synthesized via an oxiranyl anion coupling and a 6-endo cyclization, and the D-ring was forged by means of an oxidative lactonization and subsequent palladium-catalyzed functionalization of the lactone ring. In this manner, the number of linear synthetic steps required for the construction of the C- and D-rings was reduced from 22 to 11."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380004239431088515","@type":"Researcher","foaf:name":[{"@value":"Haruhiko Fuwa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004239431088521","@type":"Researcher","foaf:name":[{"@value":"Ryo Fukazawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1030003658361950337","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"80235267"},{"@type":"NRID","@value":"1000080235267"},{"@type":"NRID","@value":"9000243751243"},{"@type":"NRID","@value":"9000256026194"},{"@type":"NRID","@value":"9000257729726"},{"@type":"NRID","@value":"9000010587399"},{"@type":"NRID","@value":"9000256029660"},{"@type":"NRID","@value":"9000006766318"},{"@type":"NRID","@value":"9000019077586"},{"@type":"NRID","@value":"9000317132999"},{"@type":"NRID","@value":"9000025052798"},{"@type":"NRID","@value":"9000263064511"},{"@type":"NRID","@value":"9000006766336"},{"@type":"NRID","@value":"9000016386963"},{"@type":"NRID","@value":"9000345347978"},{"@type":"NRID","@value":"9000257731456"},{"@type":"NRID","@value":"9000010317763"},{"@type":"NRID","@value":"9000107381382"},{"@type":"NRID","@value":"9000017463033"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0092036"}],"foaf:name":[{"@value":"Makoto Sasaki"}]}],"publication":{"publicationIdentifier":[{"@type":"EISSN","@value":"22962646"}],"prism:publicationName":[{"@value":"Frontiers in Chemistry"}],"dc:publisher":[{"@value":"Frontiers Media SA"}],"prism:publicationDate":"2015-01-13","prism:volume":"2","prism:startingPage":"116"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","createdAt":"2015-01-13","modifiedAt":"2017-06-22","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=oxiranyl%20anions","dc:title":"oxiranyl anions"},{"@id":"https://cir.nii.ac.jp/all?q=palladium-catalyzed%20reactions","dc:title":"palladium-catalyzed reactions"},{"@id":"https://cir.nii.ac.jp/all?q=Oxidative%20lactonization","dc:title":"Oxidative lactonization"},{"@id":"https://cir.nii.ac.jp/all?q=Oxiranyl%20anions","dc:title":"Oxiranyl anions"},{"@id":"https://cir.nii.ac.jp/all?q=Palladium-catalyzed%20reactions","dc:title":"Palladium-catalyzed reactions"},{"@id":"https://cir.nii.ac.jp/all?q=Chemistry","dc:title":"Chemistry"},{"@id":"https://cir.nii.ac.jp/all?q=marine%20polycyclic%20ethers","dc:title":"marine polycyclic ethers"},{"@id":"https://cir.nii.ac.jp/all?q=6-endo%20cyclization","dc:title":"6-endo cyclization"},{"@id":"https://cir.nii.ac.jp/all?q=oxidative%20lactonization","dc:title":"oxidative lactonization"},{"@id":"https://cir.nii.ac.jp/all?q=Marine%20polycyclic%20ethers","dc:title":"Marine polycyclic ethers"},{"@id":"https://cir.nii.ac.jp/all?q=QD1-999","dc:title":"QD1-999"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040282257116720000","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"23102016"},{"@type":"JGN","@value":"JP23102016"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PLANNED-23102016/"}],"notation":[{"@language":"ja","@value":"ポリエーテル天然物を基盤としたイオンチャネル選択的阻害剤の創製と機能解析・制御"},{"@language":"en","@value":"Synthesis and functional analysis of ion channel selective inhibitors based on polycyclic ethers"}]},{"@id":"https://cir.nii.ac.jp/crid/1040282257217853952","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"25282228"},{"@type":"JGN","@value":"JP25282228"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-25282228/"}],"notation":[{"@language":"ja","@value":"複雑マクロリド天然物を構造基盤とする新規生体機能分子の創製と機能解析"},{"@language":"en","@value":"Synthesis and functional analysis of novel biologically active molecules based on complex macrolide natural products"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050306506459156608","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds"},{"@value":"ChemInform Abstract: Palladium‐Catalyzed Cross‐Coupling Reactions of Organoboron Compounds"},{"@value":"Palladium-catalyzed cross-coupling reaction of organoboron 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