Low-temperature vinylcyclopropane rearrangement in the total synthesis of (-) - specionin

dc.contributor.authorNatchus, Michael Georgeen
dc.contributor.committeechairHudlicky, Tomasen
dc.contributor.committeememberTanko, James M.en
dc.contributor.committeememberBecker, David A.en
dc.contributor.committeememberMason, John G.en
dc.contributor.committeememberWhite, Robert H.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:21:56Zen
dc.date.adate2005-10-21en
dc.date.available2014-03-14T21:21:56Zen
dc.date.issued1992en
dc.date.rdate2005-10-21en
dc.date.sdate2005-10-21en
dc.description.abstractThe microbial oxidation of arenes to the corresponding cis-diols has been shown to be a convenient source of optically pure diols which can be used as synthons in asymmetric synthesis of complex, highly oxygenated molecules. The utility of such synthons has been demonstrated by the total synthesis of (-)- Specionin 1. A key transformation in this sequence is a low-temperature rearrangement of vinylcyclopropane 59 to diquinanes 61 and 62. Of additional merit is the development of an efficient preparation of enone 56 from cis arene diol 66.en
dc.description.degreePh. D.en
dc.format.extentvi, 179 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-10212005-123014en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-10212005-123014/en
dc.identifier.urihttp://hdl.handle.net/10919/40075en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1992.N372.pdfen
dc.relation.isformatofOCLC# 26145479en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1992.N372en
dc.subject.lcshCyclopropaneen
dc.subject.lcshSpecionin -- Synthesisen
dc.titleLow-temperature vinylcyclopropane rearrangement in the total synthesis of (-) - specioninen
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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