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dc.contributor.advisorMinter, David E.
dc.contributor.authorSouth, Bobbie Enloe, Jr.en_US
dc.date.accessioned2019-10-11T15:10:02Z
dc.date.available2019-10-11T15:10:02Z
dc.date.created1991en_US
dc.date.issued1991en_US
dc.identifieraleph-508522en_US
dc.identifierMicrofilm Diss. 552.en_US
dc.identifier.urihttps://repository.tcu.edu/handle/116099117/31802
dc.description.abstractIn order to determine the viability of a conceptually different approach to the synthesis of quinine, a model study was initiated to synthesize all-carbon structural analogs of quinine. Thus, syn-6-vinylbicyclo (2.2.2) oct-2-one (1) was synthesized. The enolate generated from 1 and LDA was condensed with benzaldehyde and reduced in situ to give two diols in which the major isomer, resulting from addition to the enolate face opposite that of the vinyl group, predominated in a ratio of 9:1. When 7-methoxy-1-napthaldehyde was used as the electrophile, HPLC analysis indicated a selectivity of 33:1 for the major to minor isomers. The benzylic coupling constant indicated the major isomer to be threo. The enolate generated from 3-quinuclidinone and LDA was condensed with quinoline-4-carboxaldehyde and reduced in situ to give 7-hydroxydesvinylcinchonidine (2). The structure of 2 was confirmed to be the erythro, trans diole by converting it to its diacetate 3 and obtaining an x-ray crystallographic analysis of the product 3. The synthesis of syn-5-($\beta$-hydroxyethyl)-3-quinuclidinone was improved by an ortho lithiation strategy starting with isonicotinic acid anilide. syn-5-Vinyl-3-quinuclidinone was synthesized as its acetate salt from the pyrolysis of syn-5-($\beta$-acetoxy-ethyl)-3-quinuclidinone. Condensation and reduction, as in the case of 2, gave a product whose mass spectral data was consistent with formation of 7-hydroxyquinine.
dc.format.extentvi, 100 leaves : illustrationsen_US
dc.format.mediumFormat: Printen_US
dc.language.isoengen_US
dc.relation.ispartofTexas Christian University dissertationen_US
dc.relation.ispartofAS38.S659en_US
dc.subject.lcshQuinineen_US
dc.subject.lcshOrganic compounds--Synthesisen_US
dc.titleA diastereoselective approach to the total synthesis of quinineen_US
dc.typeTexten_US
etd.degree.departmentDepartment of Chemistry
etd.degree.levelDoctoral
local.collegeCollege of Science and Engineering
local.departmentChemistry and Biochemistry
local.academicunitDepartment of Chemistry
dc.type.genreDissertation
local.subjectareaChemistry and Biochemistry
dc.identifier.callnumberSpecial Collections: AS38 .S659 (Non-Circulating)
etd.degree.nameDoctor of Philosophy
etd.degree.grantorTexas Christian University


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