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Memorial University - Electronic Theses and Dissertations 2
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Document Description
TitleStudies directed toward the total synthesis of retigeranic acid
AuthorSmith, Ralph Stephen
DescriptionThesis (M.Sc.)--Memorial University of Newfoundland, 1985. Chemistry
Paginationvi, 82 leaves : ill.
SubjectRetigeranic acid; Organic acids
Degree GrantorMemorial University of Newfoundland. Dept. of Chemistry
NotesBibliography: leaves 78-82.
AbstractStudies directed at the total synthesis of retigeranic acid (1) have revealed that compounds of type 81a and 87 cyclize in intramolecular fashion to give the conjoint ring systems 91 and 90 rather than the fused bicyclo [3.3.0] octanes 48 and 88. Increasing the acidity of the Y-proton did not result in alkylative cyclization. -- The Wittig reagents 124, 125, and 126 have been synthesized and shown to react in normal fashion with aldehydes to give enol-ether-dienes such as 128 and a, p- unsaturated ketones 129 after hydrolysis. A route to a suitable triene 111 for the construction of the hydrindane portion of retigeranic acid has been developed, but unfortunately conditions were not found that allowed the intramolecular Diels-Alder reaction to proceed.
Resource TypeElectronic thesis or dissertation
FormatImage/jpeg; Application/pdf
SourcePaper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries
Local Identifier75331751
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(10.80 MB) --
CONTENTdm file name64781.cpd