Reactivity studies of arene-cis-diols in cycloadditions and potassium permanganate oxidations: synthesis of the corresponding arene-trans-diols and an approach to the synthesis of (+)-pancratistatin

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dc.contributor.authorMcKibben, Bryan P.en
dc.contributor.committeechairHudlicky, Tomasen
dc.contributor.committeememberTanko, James M.en
dc.contributor.committeememberKingston, David G. I.en
dc.contributor.committeememberMerola, Joseph S.en
dc.contributor.committeememberGandour, Richard D.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:13:43Zen
dc.date.adate2008-06-06en
dc.date.available2014-03-14T21:13:43Zen
dc.date.issued1994en
dc.date.rdate2008-06-06en
dc.date.sdate2008-06-06en
dc.description.abstractPotassium permanganate oxidations and novel cycloaddition chemistry of the arene-cis-diols (7) were investigated. It was found that permanganate oxidation of arene-cis-diols yielded a mixture of 2 products, (157a) and (157b) in low yield. The influence of the C1-substituent on the outcome of the reaction was found to be a complex mixture of steric and electronic effects. In the area of cycloaddition chemistry of protected (7), this thesis describes novel [4+2] cycloadditions with quinones along with the first published report of benzyne and nitrile oxide cycloadditions of these homochiral molecules. The structure of the cycloadducts were elucidated by nOe as well as 2D-NMR analysis and were supported by Frontier Molecular Orbital theory. Finally, arene-trans-diols (200) were synthesized from (7) by a multistep stereoselective protection/deprotection sequence utilizing the Diels-Alder reaction. These compounds serve as intermediates in an approach to the amaryllidaceae alkaloid (+)-pancratistatin (12).en
dc.description.degreePh. D.en
dc.format.extentix, 166 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-06062008-164317en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-06062008-164317/en
dc.identifier.urihttp://hdl.handle.net/10919/38267en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1994.M437.pdfen
dc.relation.isformatofOCLC# 32749118en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1994.M437en
dc.subject.lcshAromatic compoundsen
dc.subject.lcshPotassium permanganateen
dc.subject.lcshRing formation (Chemistry)en
dc.titleReactivity studies of arene-cis-diols in cycloadditions and potassium permanganate oxidations: synthesis of the corresponding arene-trans-diols and an approach to the synthesis of (+)-pancratistatinen
dc.typeDissertationen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.leveldoctoralen
thesis.degree.namePh. D.en

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