Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors

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dc.authoridGunel, Aslihan/0000-0001-5301-2628
dc.contributor.authorBaran, Arif
dc.contributor.authorGuenel, Aslihan
dc.contributor.authorBalci, Metin
dc.date.accessioned2025-03-23T19:35:48Z
dc.date.available2025-03-23T19:35:48Z
dc.date.issued2008
dc.departmentSinop Üniversitesi
dc.description.abstractFor the construction of the bicyclo[2.2.2] octane skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was reacted with vinylene carbonate to give two isomeric cycloadditon products having the bicyclo[2.2.2]octane skeleton. Hydrolysis of the ketal ring and the opening of the carbonate functionality, followed by hydroxylation of the remaining double bond resulted in the formation of a symmetrical hexol. Epoxidation of the double bond in the cycloaddition products and the subsequent ring-opening reactions produce two additional hexol derivatives. One of the synthesized molecules exhibited enzyme-specific inhibition against alpha-glycosidase.
dc.identifier.doi10.1021/jo800553u
dc.identifier.endpage4375
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.issue12
dc.identifier.pmid18489161
dc.identifier.scopus2-s2.0-45249101803
dc.identifier.scopusqualityQ2
dc.identifier.startpage4370
dc.identifier.urihttps://doi.org/10.1021/jo800553u
dc.identifier.urihttps://hdl.handle.net/11486/5939
dc.identifier.volume73
dc.identifier.wosWOS:000256757100003
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectDiels-Alder Reactions
dc.subjectStereospecific Synthesis
dc.subjectFacial Selectivity
dc.subjectConduritols
dc.subjectPolycyclitols
dc.subjectDerivatives
dc.subjectCarbasugar
dc.subjectCyclitols
dc.subjectAcid
dc.titleSynthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors
dc.typeArticle

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