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UBC Theses and Dissertations
Sulphur and selenium mediated cyclizations of β-keto esters : a novel synthetic approach to carotenoid end groups Alderdice, Margot Elaine
Abstract
The electrophilic cyclization of the β-keto ester 43 to the selenide 69 and to the sulfide 87 via different methods, was achieved. These two products were then elaborated in an attempt [diagram not included] to produce a C-2 substituted carotenoid end group moiety 14. The selenium route was discontinued, though, when difficulties in [diagram not included] alkylating the selenide 81 could not be overcome. The sulphur route proved to be more successful when the sulphoxide 98 was [diagram not included] alkylated with two different groups in the C-2 position. However, the ensuing elimination of the sulphoxide in the first [diagram not included] product and the rearrangement of the second product precluded the option of finishing the route to a carotenoid end group moiety 14 at this time. An intermediate suitable for elaboration as a C-3 hydroxy-lated carotenoid end group moiety was also prepared from both the selenium and sulphur routes.
Item Metadata
Title |
Sulphur and selenium mediated cyclizations of β-keto esters : a novel synthetic approach to carotenoid end groups
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
1980
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Description |
The electrophilic cyclization of the β-keto ester 43 to the selenide 69 and to the sulfide 87 via different methods, was achieved. These two products were then elaborated in an attempt [diagram not included] to produce a C-2 substituted carotenoid end group moiety 14. The selenium route was discontinued, though, when difficulties in [diagram not included] alkylating the selenide 81 could not be overcome. The sulphur route proved to be more successful when the sulphoxide 98 was [diagram not included] alkylated with two different groups in the C-2 position. However, the ensuing elimination of the sulphoxide in the first [diagram not included] product and the rearrangement of the second product precluded the option of finishing the route to a carotenoid end group moiety 14 at this time. An intermediate suitable for elaboration as a C-3 hydroxy-lated carotenoid end group moiety was also prepared from both the selenium and sulphur routes.
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Genre | |
Type | |
Language |
eng
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Date Available |
2010-03-17
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Provider |
Vancouver : University of British Columbia Library
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Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
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DOI |
10.14288/1.0059424
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URI | |
Degree | |
Program | |
Affiliation | |
Degree Grantor |
University of British Columbia
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Campus | |
Scholarly Level |
Graduate
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Aggregated Source Repository |
DSpace
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Item Media
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Rights
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.