{"@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/1363388844484351232.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1016/0040-4020(95)00758-z"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:004040209500758Z?httpAccept=text/xml"}},{"identifier":{"@type":"URI","@value":"https://api.elsevier.com/content/article/PII:004040209500758Z?httpAccept=text/plain"}},{"identifier":{"@type":"NAID","@value":"30004193261"}}],"dc:title":[{"@value":"Chemo-enzymatic synthesis of (R,R)-(-)-Pyrenophorin"}],"description":[{"notation":[{"@value":"Abstract   A chemo-enzymatic approach to (R,R)-(-)-pyrenophorin starting from commercially available 6-methyl-5-hepten-2-one is described. Firstly, (R)-6-methyl-5-hepten-2-ol (sulcatol) was prepared by interface-bioreactor mediated asymmetric reduction of the corresponding ketone by a yeast, Pichia farinosa IAM 4682 (51% yield, 90%e.e.). The sequential carbon-chain elongation via Horner-Emmons olefination of protected aldehyde and cyanation afforded all of carbon skeleton in the seco acid with a desired β,γ-(E)-double bond. By the aid of a microorganism, Rhodococcus rhodochrous IFO15564, the nitrile was efficiently hydrolyzed to give the corresponding carboxylic acid, (R,E)-7-hydroxy-3-octenoate, the key synthetic intermediate without affecting the position and configuration of the double bond (90% yield). Dimeric lactone structure was obtained by utilizing a lipase-catalyzed lactonization. While Pseudomonas cepacia lipase-catalyzed reaction worked in a moderate efficiency, higher yield of desired dimeric lactone (44%) was obtained by the use of an immobilized form of Candida antarctica lipase. The lactonization was accelerated in the presence of molecular sieves 4A. (R,R)-(-)-Pyrenophorin was obtained from this dimeric lactone (Seebach's intermediate) by the subsequent chemical transformation."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1420845751141389824","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"60171120"},{"@type":"NRID","@value":"1000060171120"},{"@type":"NRID","@value":"9000259321991"},{"@type":"NRID","@value":"9000402379968"},{"@type":"NRID","@value":"9000345335565"},{"@type":"NRID","@value":"9000406179629"},{"@type":"NRID","@value":"9000399599829"},{"@type":"NRID","@value":"9000021905073"},{"@type":"NRID","@value":"9000414201524"},{"@type":"NRID","@value":"9000401960438"},{"@type":"NRID","@value":"9000256031609"},{"@type":"NRID","@value":"9000356653754"},{"@type":"NRID","@value":"9000007039826"},{"@type":"NRID","@value":"9000401542905"},{"@type":"NRID","@value":"9000020874740"},{"@type":"NRID","@value":"9000283372272"},{"@type":"NRID","@value":"9000403046085"},{"@type":"NRID","@value":"9000383074164"},{"@type":"NRID","@value":"9000398791782"},{"@type":"NRID","@value":"9000309993357"},{"@type":"NRID","@value":"9000020792728"},{"@type":"NRID","@value":"9000020840110"},{"@type":"NRID","@value":"9000006432391"},{"@type":"NRID","@value":"9000256015639"},{"@type":"NRID","@value":"9000326648752"},{"@type":"NRID","@value":"9000401959542"},{"@type":"NRID","@value":"9000256013216"},{"@type":"NRID","@value":"9000256042966"},{"@type":"NRID","@value":"9000021019687"},{"@type":"NRID","@value":"9000326650729"},{"@type":"NRID","@value":"9000356877978"},{"@type":"NRID","@value":"9000265565262"},{"@type":"NRID","@value":"9000401542409"},{"@type":"NRID","@value":"9000020749091"},{"@type":"NRID","@value":"9000019947285"},{"@type":"NRID","@value":"9000257702473"},{"@type":"NRID","@value":"9000403046073"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0024859"}],"foaf:name":[{"@value":"Takeshi Sugai"}]},{"@id":"https://cir.nii.ac.jp/crid/1383388844484351361","@type":"Researcher","foaf:name":[{"@value":"Osamu Katoh"}]},{"@id":"https://cir.nii.ac.jp/crid/1383388844484351362","@type":"Researcher","foaf:name":[{"@value":"Hiromichi Ohta"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00404020"}],"prism:publicationName":[{"@value":"Tetrahedron"}],"dc:publisher":[{"@value":"Elsevier BV"}],"prism:publicationDate":"1995-10","prism:volume":"51","prism:number":"44","prism:startingPage":"11987","prism:endingPage":"11998"},"reviewed":"false","dc:rights":["https://www.elsevier.com/tdm/userlicense/1.0/","https://www.elsevier.com/legal/tdmrep-license"],"url":[{"@id":"https://api.elsevier.com/content/article/PII:004040209500758Z?httpAccept=text/xml"},{"@id":"https://api.elsevier.com/content/article/PII:004040209500758Z?httpAccept=text/plain"}],"createdAt":"2002-07-25","modifiedAt":"2025-11-03","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360283694085881472","@type":"Article","relationType":["isReferencedBy","isCitedBy"],"jpcoar:relatedTitle":[{"@value":"Biocatalytic Preparation of (<i>R</i>)-(−)-4-(Phenylthio)-2-butanol and (<i>R</i>)-(−)-4-(Phenylsulfonyl)-2-butanol by the Sequential Use of <i>Pichia farinosa and Rhodococcus rhodochrous</i>"}]},{"@id":"https://cir.nii.ac.jp/crid/1360283694086327680","@type":"Article","relationType":["isReferencedBy","isCitedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of (<i>R</i>c,<i>S</i>s)-1,1,1-Trifluoro-3-(<i>p</i>-tolylsulfinyl)-2-propanol by an Asymmetric Reduction with a Yeast, <i>Yamadazyma farinosa</i>, as a Key-step"}]},{"@id":"https://cir.nii.ac.jp/crid/1360284919608123904","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of methyl ursodeoxycholate via microbial reduction of methyl 7-ketolithocholate with Eubacterium aerofaciens JCM 7790 grown on two kinds of carbon and hydride sources, glucose and mannitol"}]},{"@id":"https://cir.nii.ac.jp/crid/1360565169062821376","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Pivotal Role of (<i>E</i>)-3-Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions: Synthesis of (<i>3E</i>,<i>5E</i>)- and (<i>3E</i>,<i>5Z</i>)-6-Phenyl-3,5-hexadienoic Acid"}]},{"@id":"https://cir.nii.ac.jp/crid/1360566394584835584","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Preparation of methyl ursodeoxycholate via microbial reduction of methyl 7-ketolithocholate in an anaerobic interface bioreactor"}]},{"@id":"https://cir.nii.ac.jp/crid/1390001204121504896","@type":"Article","relationType":["isReferencedBy","isCitedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction as the Key Step."},{"@language":"ja-Kana","@value":"Preparation of Sulfur-Containing Optica"},{"@value":"Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on <i>Pichia farinosa</i>-Catalyzed <i>anti</i>-Prelog-Rule Reduction as the Key Step"},{"@value":"ChemInform Abstract: Preparation of Sulfur‐Containing 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