Please use this identifier to cite or link to this item: http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2669
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dc.contributor.authorKaranfil, Abdullah-
dc.contributor.authorKelebekli, Latif-
dc.contributor.authorSahin, Ertan-
dc.date.accessioned2022-08-17T07:03:43Z-
dc.date.available2022-08-17T07:03:43Z-
dc.date.issued2020-
dc.identifier.urihttp://doi.org/10.1016/j.tet.2020.131000-
dc.identifier.urihttp://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2669-
dc.description.abstractThe synthesis of halogenated bicyclo[4.2.01 inositols (and/or tetrols) are described. The photooxygenation of trans-7,8-dibromobicyclo[4.2.01octa-2,4-diene obtained using cyclooctatetraene as the starting molecule afforded the bicyclic endoperoxide. To obtain the halogenated bicyclo[4.2.0] inositols, the required key intermediate endoperoxide was rearranged quantitatively to the corresponding bisepoxide under thermal conditions. Ring-opening reaction of the bisepoxide with H+/Ac2O resulted in a mixture of tetraacetates as well as the formation of a cyclic sulfate. Eventually, the desired halogenated bicyclo[4.2.0] inositols (and/or tetrols) were obtained in high yield by ammonolysis of the acetate groups by NH3. The structures of all the synthesized compounds were characterized by spectroscopic methods. (C) 2020 Elsevier Ltd. All rights reserved.en_US
dc.language.isoengen_US
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDen_US
dc.relation.isversionof10.1016/j.tet.2020.131000en_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectCyclitol; Tetrol; Halogenated cyclitol; Ring-opening of syn-bisepoxide; Cyclic sulfateen_US
dc.subjectENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; MOLECULAR COMPLEXITY; CYCLIC SULFATES; CYCLOOCTATETRAENE; DERIVATIVES; EPOXIDES; REARRANGEMENT; NARCICLASINE; GLUCOSIDASEen_US
dc.titleSynthesis of novel tetrols from syn-bisepoxide: Preparation of halogenated bicyclo[4.2.0] inositolsen_US
dc.typearticleen_US
dc.relation.journalTETRAHEDRONen_US
dc.contributor.departmentOrdu Üniversitesien_US
dc.contributor.authorID0000-0003-2948-4216en_US
dc.identifier.volume76en_US
dc.identifier.issue11en_US
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