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dc.contributor.advisorMinter, David E.
dc.contributor.authorLindabery, Gregory C.en_US
dc.date.accessioned2019-10-11T15:10:03Z
dc.date.available2019-10-11T15:10:03Z
dc.date.created1999en_US
dc.date.issued1999en_US
dc.identifieraleph-814392en_US
dc.identifier.urihttps://repository.tcu.edu/handle/116099117/31830
dc.description.abstractIn an effort to develop an efficient synthetic route to the crinane skeleton from isoquinoline, an unprecedented conversion, several novel reactions have been discovered and explored. N-Benzyl-4,4dialkyldihydroisoquinolmium salts, which can be readily prepared from isoquinoline by utilizing boron-activated enamine alkylation chemistry, undergo facile oxidation with m-chloroperoxybenzoic, acid to afford 3-hydroxy-1-isoquinolones and the corresponding homophthalimides; regioselective sodium borohydride reduction of the latter affords the former. Treatment of 3-hydroxy-1-isoquinolones with sulfinic acid results in the formation of isocarbostyrils by dealkylation or acid-catalyzed dehydrative alkyl migration. In the caw of the 4-spirobutyl system, this reaction sequence represents an efficient entry to the relatively inaccessible 1,2,3,4-tetrahydrophenanthridine nucleus of the crinine, narciclasine, and lycorine type alkaloids.en_US
dc.format.extentx, 249 leaves : illustrationsen_US
dc.format.mediumFormat: Printen_US
dc.language.isoengen_US
dc.relation.ispartofTexas Christian University dissertationen_US
dc.relation.ispartofAS38.L56en_US
dc.subject.lcshIsoquinolineen_US
dc.subject.lcshAlkaloidsen_US
dc.titleNovel synthetic approaches to the 5,10b-ethano-phenanthridine nucleus of the crinine-type amaryllidaceae alkaloids from isoquinolineen_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.callnumberMain Stacks: AS38 .L56 (Regular Loan)
dc.identifier.callnumberSpecial Collections: AS38 .L56 (Non-Circulating)
etd.degree.nameDoctor of Philosophy
etd.degree.grantorTexas Christian University


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