dc.contributor.advisor | Minter, David E. | |
dc.contributor.author | Lindabery, Gregory C. | en_US |
dc.date.accessioned | 2019-10-11T15:10:03Z | |
dc.date.available | 2019-10-11T15:10:03Z | |
dc.date.created | 1999 | en_US |
dc.date.issued | 1999 | en_US |
dc.identifier | aleph-814392 | en_US |
dc.identifier.uri | https://repository.tcu.edu/handle/116099117/31830 | |
dc.description.abstract | In 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. | |
dc.format.extent | x, 249 leaves : illustrations | en_US |
dc.format.medium | Format: Print | en_US |
dc.language.iso | eng | en_US |
dc.relation.ispartof | Texas Christian University dissertation | en_US |
dc.relation.ispartof | AS38.L56 | en_US |
dc.subject.lcsh | Isoquinoline | en_US |
dc.subject.lcsh | Alkaloids | en_US |
dc.title | Novel synthetic approaches to the 5,10b-ethano-phenanthridine nucleus of the crinine-type amaryllidaceae alkaloids from isoquinoline | en_US |
dc.type | Text | en_US |
etd.degree.department | Department of Chemistry | |
etd.degree.level | Doctoral | |
local.college | College of Science and Engineering | |
local.department | Chemistry and Biochemistry | |
local.academicunit | Department of Chemistry | |
dc.type.genre | Dissertation | |
local.subjectarea | Chemistry and Biochemistry | |
dc.identifier.callnumber | Main Stacks: AS38 .L56 (Regular Loan) | |
dc.identifier.callnumber | Special Collections: AS38 .L56 (Non-Circulating) | |
etd.degree.name | Doctor of Philosophy | |
etd.degree.grantor | Texas Christian University | |