Facile Synthesis of Highly Functionalized Bicyclo[3.2.1]octanes as Building Blocks for Various Natural Products

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dc.contributor.authorHadjiarapoglou, L.;en
dc.contributor.authorde Meijere, A.;en
dc.contributor.authorSeitz, H.-J.;en
dc.contributor.authorKlein, I.;en
dc.contributor.authorSpitzner, D.en
dc.date.accessioned2015-11-24T16:58:25Z
dc.date.available2015-11-24T16:58:25Z
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/10686
dc.rightsDefault Licence-
dc.titleFacile Synthesis of Highly Functionalized Bicyclo[3.2.1]octanes as Building Blocks for Various Natural Productsen
heal.abstractThe cascade cycloaddition of 1-alkoxycyclohexadienolates 2 onto 2-chloro-2-cyclopropylideneacetate 4 yields 2-alkoxytricyclo[3.2.1.02.7octane-2,6-diones 8 under acid catalysis. The tricyclooctanones 7 can be further elaborated, e. g. by Wittig olefination and reduction of the carbonyl group, or deprotonation at the bridgehead C-7 with subsequent alkylation, acylation or aldol reaction, before they are rearranged to the highly functionalized bicyclo[3.2.1]octane derivatives 10, 11, 13, and 17, respectively. The diones 8 can also be further manipulated, e. g. by regioselective Wittig olefination at C-2.en
heal.accesscampus-
heal.fullTextAvailabilityTRUE-
heal.identifier.secondaryhttp://www.sciencedirect.com/science/article/pii/S0040403900768821-
heal.journalNameTetrahedron Letten
heal.journalTypepeer reviewed-
heal.languageen-
heal.publicationDate1994-
heal.publisherElsevieren
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.typejournalArticle-
heal.type.elΆρθρο Περιοδικούel
heal.type.enJournal articleen

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