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Memorial University - Electronic Theses and Dissertations 1
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Document Description
TitleStudies directed toward the total synthesis of longifolene
AuthorBukownik, Rudolf Robert
DescriptionThesis (M.Sc.) -- Memorial University of Newfoundland, 1985. Chemistry
Date1984
Paginationvii, 60 leaves : ill.
SubjectTerpenes--Synthesis; Diels-Alder reaction;
DegreeM.Sc.
Degree GrantorMemorial University of Newfoundland. Dept. of Chemistry
DisciplineChemistry
LanguageEng
NotesBibliography : leaves 58-60.
AbstractThis thesis describes studies directed toward the total synthesis of longifolene utilizing as a key step an intramolecular Diels-Alder cyclization. Different approaches for the construction of spiro[2.4]hepta-4, 6-dienes have been explored and a general route involving the fulvene 63 developed. Nucleophilic addition of methlylithium to this fulvene generates a cyclopentadiene anion in situ, which closes to the requisite cyclopropane system by epoxide ring opening to afford 65. This cyclopentadiene unit will thus serve as the ‘left-had portion' for the approach to longifolene which is outlined. Procedures for the preparation and introduction of a suitable ‘right-hand portion' have also been examined, these preliminary results have indicated the subtle blend of functionality and reactivity that will be required to generate the dienophilic unit. A suitable triene system 104 was synthesized (unfortunately in low yield) but under the conditions examined the desired Diels-Alder cyclization did not occur.
TypeText
Resource TypeElectronic thesis or dissertation
FormatImage/jpeg; Application/pdf
SourcePaper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries
Local Identifier75331813
RightsThe author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
CollectionElectronic Theses and Dissertations
Scanning StatusCompleted
PDF File(21.56 MB) -- http://collections.mun.ca/PDFs/theses/Bukownik_RudolfRobert.pdf
CONTENTdm file name312659.cpd