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College of Natural Sciences(자연과학대학)Dept. of Chemistry(화학과)CH-Journal Papers(저널논문)

Total synthesis of laidlomycin

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dc.contributor.authorLee, Wonchulko
dc.contributor.authorKang, Sungkyoungko
dc.contributor.authorJung, Byunghyuckko
dc.contributor.authorLee, Hee-Seungko
dc.contributor.authorKang, Sung Hoko
dc.date.accessioned2016-06-07T08:58:25Z-
dc.date.available2016-06-07T08:58:25Z-
dc.date.created2016-02-05-
dc.date.created2016-02-05-
dc.date.issued2016-02-
dc.identifier.citationCHEMICAL COMMUNICATIONS, v.52, no.17, pp.3536 - 3539-
dc.identifier.issn1359-7345-
dc.identifier.urihttp://hdl.handle.net/10203/207656-
dc.description.abstractThe synthesis of laidlomycin is described. With an established stereocontrolled synthetic route to the aldehyde 5, the known beta-keto phosphonate 4 was coupled with 5 and the resulting enone was subjected to a sequential hydrogenolysis/hydrogenation and equilibration process to effect the correct spiroketalization for the natural product. The stereogenic carbons were elaborated by desymmetrization for C12, allylation for C13, vanadyl-induced epoxidation for C16, Zn(BH4)(2) reduction for C17, a chiral building block for C18 and C24, Shi epoxidation for C20 and C21, Myers' alkylation for C22, and thermodynamic control for C25.-
dc.languageEnglish-
dc.publisherROYAL SOC CHEMISTRY-
dc.subjectSTEREOCONTROLLED TOTAL-SYNTHESIS-
dc.subjectPOLYETHER ANTIBIOTICS-
dc.subjectASYMMETRIC EPOXIDATION-
dc.subjectOXIDATIVE CYCLIZATION-
dc.subjectZINC BOROHYDRIDE-
dc.subjectCARBOXYLIC-ACIDS-
dc.subjectNATURAL-PRODUCTS-
dc.subjectMETHYL-ESTERS-
dc.subjectALCOHOLS-
dc.subjectMONENSIN-
dc.titleTotal synthesis of laidlomycin-
dc.typeArticle-
dc.identifier.wosid000371026700019-
dc.identifier.scopusid2-s2.0-84959162139-
dc.type.rimsART-
dc.citation.volume52-
dc.citation.issue17-
dc.citation.beginningpage3536-
dc.citation.endingpage3539-
dc.citation.publicationnameCHEMICAL COMMUNICATIONS-
dc.identifier.doi10.1039/C5CC10673G-
dc.contributor.localauthorLee, Hee-Seung-
dc.contributor.localauthorKang, Sung Ho-
dc.contributor.nonIdAuthorJung, Byunghyuck-
dc.type.journalArticleArticle-
dc.subject.keywordPlusSTEREOCONTROLLED TOTAL-SYNTHESIS-
dc.subject.keywordPlusPOLYETHER ANTIBIOTICS-
dc.subject.keywordPlusASYMMETRIC EPOXIDATION-
dc.subject.keywordPlusOXIDATIVE CYCLIZATION-
dc.subject.keywordPlusZINC BOROHYDRIDE-
dc.subject.keywordPlusCARBOXYLIC-ACIDS-
dc.subject.keywordPlusNATURAL-PRODUCTS-
dc.subject.keywordPlusMETHYL-ESTERS-
dc.subject.keywordPlusALCOHOLS-
dc.subject.keywordPlusMONENSIN-
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CH-Journal Papers(저널논문)
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