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UBC Theses and Dissertations
Synthesis and reactions of unsaturated 14-membered lactones Leslie, Ray
Abstract
Via a lactonization of the open chain hydroxy acid, the 14-membered unsaturated lactones 14 and 15 were synthesised. Treatment of these two lactones with borane dimethylsulphide, disiamyl borane and 9BBN led to formationof hydroxy lactones 30, 31, 32 and 33. The structures of 31 and 32 were determined by comparison with known compounds whereas structures 30 and 33 were deduced by considering the transition structures of the hydroboration reaction. Although both the regio and the stereoselectivity of the reactions were poor the π-face selectivity was high. Product distributions were estimated by the conformational control induced by the ring, using Houk's parameters for the hydroboration transition structures, in an MM2 force field, to calculate their relative strain energies. [ formulas omitted]
Item Metadata
Title |
Synthesis and reactions of unsaturated 14-membered lactones
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
1991
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Description |
Via a lactonization of the open chain hydroxy acid, the 14-membered unsaturated lactones 14 and 15 were synthesised. Treatment of these two lactones with borane dimethylsulphide, disiamyl borane and 9BBN led to formationof hydroxy lactones 30, 31, 32 and 33. The structures of 31 and 32 were determined by comparison with known compounds whereas structures 30 and 33 were deduced by considering the transition structures of the hydroboration reaction. Although both the regio and the stereoselectivity of the reactions were poor the π-face selectivity was high. Product distributions were estimated by the conformational control induced by the ring, using Houk's parameters for the hydroboration transition structures, in an MM2 force field, to calculate their relative strain energies.
[ formulas omitted]
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Genre | |
Type | |
Language |
eng
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Date Available |
2010-11-18
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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 |
10.14288/1.0059728
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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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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.