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dc.contributor.advisorMartin, Stephen F.
dc.creatorProcko, Kristen Jeanen 2009en
dc.description.abstractIn the context of ongoing efforts toward C-aryl glycoside synthesis, a recently developed approach to form C-aryl glycals from 2-deoxysugar lactones was expanded to form novel substrates. This approach has been applied to the synthesis of various furyl glycals, allowing access to C-aryl glycals via a benzyne furan (4+2) cycloaddition methodology. The hydroboration-oxidation of said C-aryl glycals has allowed access to C(2)-oxygenated C-aryl glycosides via the benzyne cycloaddition approach. An approach to the total synthesis of 5-hydoxyaloin A is detailed, in which regioselective benzyne furan (4+2) cycloadditions were achieved via the use of a silicon tether. Two approaches to the anthrone core have been applied; one in which an unsymmetrically-substituted aryl ring is first constructed by means of a silicon tether, and one in which the unsymmetrically-substituted ring is formed last, also utilizing a silicon tether. The latter approach has allowed access to the anthrone core of 5-hydroxyaloin A, and only a final desulfurization remains in order to access the natural product.en
dc.subjectC-aryl glycosideen
dc.subjectBenzyne-furan cycloadditionen
dc.subject(4+2) cycloadditionen
dc.subjectFuryl glycalen
dc.subjectSilicon tetheren
dc.subject5-hydroxyaloin Aen
dc.subjectRegioselective cycloadditionen
dc.subjectDirected ring openingen
dc.titleFunctionalization of C-aryl glycals and studies toward the total synthesis of 5-hydroxyaloin Aen

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