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dc.contributor.advisorMash, Eugeneen_US
dc.contributor.authorMath, Shivanand Kumarswamy.
dc.creatorMath, Shivanand Kumarswamy.en_US
dc.date.accessioned2011-10-31T17:14:54Z
dc.date.available2011-10-31T17:14:54Z
dc.date.issued1989en_US
dc.identifier.urihttp://hdl.handle.net/10150/184664
dc.description.abstractA general straightforward synthetic approach for the enantioselective construction of medium and large ring cyclopropyl ketones via diastereoselective Simmons-Smith cyclopropanation is discussed. Medium and large 2-cycloalkenone 1,4Di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent. The cyclopropyl ketals are obtained in 80-94% with >23:1-8:1 diastereoselectivity. The first enantioselective synthesis of (-)-modhephene, a natural product possessing the carbocyclic (3.3.3) propellane skeleton, by the use of diastereoselective cyclopropanation methodology is described.
dc.language.isoenen_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.subjectStereochemistry.en_US
dc.subjectNatural products -- Synthesis.en_US
dc.subjectKetones -- Synthesis.en_US
dc.titleDiastereoselective cyclopropanation of medium and large ring alpha, beta-unsaturated homochiral ketals and enantioselective synthesis of (-)-modhephene.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.identifier.oclc702156085en_US
thesis.degree.grantorUniversity of Arizonaen_US
thesis.degree.leveldoctoralen_US
dc.contributor.committeememberLaw, Johnen_US
dc.contributor.committeememberBurke, Michaelen_US
dc.contributor.committeememberBates, Roberten_US
dc.contributor.committeememberSteelink, Corneliusen_US
dc.identifier.proquest8915973en_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.namePh.D.en_US
dc.description.noteDigitization note: Original document not clear, scans are faithful to the paper original.
refterms.dateFOA2018-08-22T20:13:21Z
html.description.abstractA general straightforward synthetic approach for the enantioselective construction of medium and large ring cyclopropyl ketones via diastereoselective Simmons-Smith cyclopropanation is discussed. Medium and large 2-cycloalkenone 1,4Di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent. The cyclopropyl ketals are obtained in 80-94% with >23:1-8:1 diastereoselectivity. The first enantioselective synthesis of (-)-modhephene, a natural product possessing the carbocyclic (3.3.3) propellane skeleton, by the use of diastereoselective cyclopropanation methodology is described.


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