A new and efficient chemoenzymatic route to both enantiomers of a-acetoxy and a-hydroxy-a-methoxy cyclic enones

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dc.contributor.authorDemir, AS
dc.contributor.authorCaliskan, Z
dc.contributor.authorAydin, AE
dc.contributor.authorBicer, I
dc.date.accessioned2024-09-18T21:03:10Z
dc.date.available2024-09-18T21:03:10Z
dc.date.issued2006
dc.departmentHatay Mustafa Kemal Üniversitesien_US
dc.description.abstractA chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP afforded (+)-4b and (-)-3b in high enantiomeric excesses (91-94%) and good chemical yields. (c) 2006 Elsevier Ltd All rights reserved.en_US
dc.identifier.doi10.1016/j.tetasy.2006.01.025
dc.identifier.endpage791en_US
dc.identifier.issn0957-4166
dc.identifier.issue5en_US
dc.identifier.scopus2-s2.0-33645833444en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage786en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2006.01.025
dc.identifier.urihttps://hdl.handle.net/20.500.12483/13287
dc.identifier.volume17en_US
dc.identifier.wosWOS:000236986100010en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectManganese(Iii) Acetateen_US
dc.subjectStereoselective Synthesisen_US
dc.subjectAsymmetric-Synthesisen_US
dc.subjectOxidationen_US
dc.subjectCombinationen_US
dc.subjectDerivativesen_US
dc.subjectAcyloxyen_US
dc.subjectKetonesen_US
dc.subjectDiosphenolsen_US
dc.subjectAciden_US
dc.titleA new and efficient chemoenzymatic route to both enantiomers of a-acetoxy and a-hydroxy-a-methoxy cyclic enonesen_US
dc.typeArticleen_US

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