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UBC Theses and Dissertations
Total synthesis of streptonigrone Chan, Bryan Ka Ip
Abstract
This thesis describes the total synthesis of streptonigrone. The centerpiece of our route to the target molecule is a facile one-pot construction of 3-alkylpyridones developed in our laboratory. The quinoline segment of the target molecule, prepared through a Conrad-Limpach synthesis, was condensed with 2-benzyloxy-3,4-dimethoxybenzaldehyde to afford a chalcone intermediate suitable for our pyridine-forming reaction. The assembly of the central 3-methylpyridone ring of the natural product was then accomplished through the merger of the chalcone with 2-cyanopropanamide. Functionalization of the pyridone was then completed through an anionic sequence.
Item Metadata
Title |
Total synthesis of streptonigrone
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
2007
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Description |
This thesis describes the total synthesis of streptonigrone. The centerpiece of our route to the target molecule is a facile one-pot construction of 3-alkylpyridones developed in our laboratory. The quinoline segment of the target molecule, prepared through a Conrad-Limpach synthesis, was condensed with 2-benzyloxy-3,4-dimethoxybenzaldehyde to afford a chalcone intermediate suitable for our pyridine-forming reaction. The assembly of the central 3-methylpyridone ring of the natural product was then accomplished through the merger of the chalcone with 2-cyanopropanamide. Functionalization of the pyridone was then completed through an anionic sequence.
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Genre | |
Type | |
Language |
eng
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Date Available |
2011-02-21
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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 |
10.14288/1.0059779
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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
Item Citations and Data
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.