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Chemistry of oxa- and aza-bicyclic(4.1.0)heptenes, total synthesis of (+)-pancratistatin

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dc.contributor.authorTian, Xinrongen
dc.contributor.committeechairHudlicky, Tomasen
dc.contributor.committeememberGibson, Harry W.en
dc.contributor.committeememberHanson, Brian E.en
dc.contributor.committeememberTanko, James M.en
dc.contributor.committeememberWhite, Robert H.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:13:30Zen
dc.date.adate2008-06-06en
dc.date.available2014-03-14T21:13:30Zen
dc.date.issued1995en
dc.date.rdate2008-06-06en
dc.date.sdate2008-06-06en
dc.description.abstractVinyloxiranes 6a-b and vinylaziridines 7a-b were prepared efficiently from halocyclohexadiene-cis-diols 1. Reactions of 6 and 7 with a variety of organometallic reagents were investigated in order to determine the stereo- and regiochemistry of ring opening with carbon nucleophiles. The results indicate that 6 and 7 could serve as useful new synthons for C-disaccharides and Amaryllidaceae alkaloid syntheses. The utility of synthon 7b has been demonstrated by a concise enantiocontrolled synthesis of (+)-pancratistatin (9). The key step involved the S<sub>N</sub>2 opening of 7b with the aryl cyanocuprate derived from amide 217 to generate the pivotal cyclization precursor.en
dc.description.degreePh. D.en
dc.format.extentx, 156 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-06062008-163626en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-06062008-163626/en
dc.identifier.urihttp://hdl.handle.net/10919/38237en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1995.T536.pdfen
dc.relation.isformatofOCLC# 33191068en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1995.T536en
dc.titleChemistry of oxa- and aza-bicyclic(4.1.0)heptenes, total 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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