{"@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/1390282679098452736.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1246/bcsj.69.2281"}},{"identifier":{"@type":"NDL_BIB_ID","@value":"4060549"}},{"identifier":{"@type":"URI","@value":"http://id.ndl.go.jp/bib/4060549"}},{"identifier":{"@type":"URI","@value":"https://ndlsearch.ndl.go.jp/books/R000000004-I4060549"}},{"identifier":{"@type":"URI","@value":"https://academic.oup.com/bcsj/article-pdf/69/8/2281/56196388/bcsj.69.2281.pdf"}},{"identifier":{"@type":"NAID","@value":"130004057977"}},{"identifier":{"@type":"NAID","@value":"10008907306"}}],"dc:title":[{"@language":"en","@value":"Simple Synthesis of <i>trans</i>-<i>α</i>,<i>β</i>-Dibenzyl-<i>γ</i>-butyrolactone Lignans by Diastereoselective Reduction of <i>α</i>-Benzylidene-<i>β</i>-benzyl-<i>γ</i>-butyrolactones Using NaBH<sub>4</sub>–NiCl<sub>2</sub>"},{"@value":"Simple Synthesis of trans-α,β-Dibenzyl-γ-butyrolactone Lignans by Diastereoselective Reduction of α-Benzylidene-β-benzyl-γ-butyrolactones Using NaBH4-NiCl2"},{"@language":"ja-Kana","@value":"Simple Synthesis of trans アルファ ベータ Dibe"},{"@value":"Simple Synthesis of <i>trans</i>-<i>α</i>,<i>β</i>-Dibenzyl-<i>γ</i>-butyrolactone Lignans by Diastereoselective Reduction of <i>α</i>-Benzylidene-<i>β</i>-benzyl-<i>γ</i>-butyrolactones Using NaBH4–NiCl2"}],"dc:language":"en","description":[{"type":"abstract","notation":[{"@language":"en","@value":"<i>trans</i>-<i>α</i>,<i>β</i>-Dibenzyl-<i>γ</i>-butyrolactone lignans were synthesized by stereoselective reduction of <i>α</i>-benzylidene-<i>β</i>-benzyl-<i>γ</i>-butyrolactones using NaBH<sub>4</sub>–NiCl<sub>2</sub>. The reduction is found to proceed via conjugate addition of a hydride to an <i>α</i>-benzylidene-<i>β</i>-benzyl-<i>γ</i>-butyrolactone and the stereoselective protonation of the resulting metal enolate. The stereoselectivity would be brought about by the conformational rigidity of the phenyl moiety of the <i>α</i>-benzyl group induced by 1,3-allylic strain."}],"abstractLicenseFlag":"disallow"}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1410282679098452739","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000255698977"},{"@type":"NRID","@value":"9000000798920"}],"foaf:name":[{"@language":"en","@value":"Moritani Yasunori"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd."},{"@language":"ja","@value":"Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679098452736","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000255698978"},{"@type":"NRID","@value":"9000000798923"}],"foaf:name":[{"@language":"en","@value":"Fukushima Chiaki"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Tanabe Seiyaku Co., Ltd."},{"@language":"ja","@value":"Tanabe Seiyaku Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679098452738","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000255698979"},{"@type":"NRID","@value":"9000000798926"}],"foaf:name":[{"@language":"en","@value":"Miyagishima Toshikazu"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Tanabe Seiyaku Co., Ltd."},{"@language":"ja","@value":"Tanabe Seiyaku Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679098452740","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000255698980"},{"@type":"NRID","@value":"9000000798929"}],"foaf:name":[{"@language":"en","@value":"Ohmizu Hiroshi"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd."},{"@language":"ja","@value":"Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679098452737","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000255698981"},{"@type":"NRID","@value":"9000000798931"}],"foaf:name":[{"@language":"en","@value":"Iwasaki Tameo"}],"jpcoar:affiliationName":[{"@language":"en","@value":"R&D Planning Division, Tanabe Seiyaku Co., Ltd."},{"@language":"ja","@value":"R&D Planning Division, Tanabe Seiyaku Co., Ltd."}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00092673"},{"@type":"LISSN","@value":"00092673"},{"@type":"EISSN","@value":"13480634"},{"@type":"NDL_BIB_ID","@value":"000000118949"},{"@type":"ISSN","@value":"00092673"},{"@type":"NCID","@value":"AA00580132"}],"prism:publicationName":[{"@language":"en","@value":"Bulletin of the Chemical Society of Japan"},{"@language":"en","@value":"Bull. 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