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UBC Theses and Dissertations
Some aspects of natural products chemistry Yalpani, Mohamed
Abstract
In part I of this thesis are described some studies toward the total synthesis of tetracycline. Attempts to transform the key aromatic compounds, terrarubein and 6-methylpretetramid into actual or hypothetical biosynthetic intermediates, failed to yield useful non-aromatic products. However, several of the transformations further along the route have been achieved. Thus, the conversion of 12a-deoxy-5a,6-anhydrotetracycline into 7-chloro-5a,6-anhydrotetracycline was successfully carried out. In a different approach it was attempted to convert the synthetic tetracycline derivative 7-chloro-4-dedimethylamino-5a,6-anhydrotetracycline to 7-chloro-5a,6-anhydrotetracycline via a series of bromination-aminatipn experiments. Chromatographic evidence is presented for the formation, in trace amounts, of 7-chloro-5a,6-anhydro-4-epi-tetracycline. Part II is concerned with the study of the possible precursor activity of triacetic acid lactone, a potential polyketomethylene chain intermediate in the biosynthesis of aromatic compounds. (3,5-¹⁴ C) Triacetic acid lactone was fed to P. patulum and labelled griseofulvin was isolated and degraded. It was found that radioactivity is incorporated into griseofulvin a non-specific way. In one strain of the mould used two new metabolites were found as a result of the addition of triacetic acid lactone. Addition of triacetic acid lactone to the mould also causes an unexplained enhancement of metabolite formation.
Item Metadata
Title |
Some aspects of natural products chemistry
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
1965
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Description |
In part I of this thesis are described some studies toward the total synthesis of tetracycline.
Attempts to transform the key aromatic compounds, terrarubein and 6-methylpretetramid into actual or hypothetical biosynthetic intermediates, failed to yield useful non-aromatic products. However, several of the transformations further along the route have been achieved. Thus, the conversion of 12a-deoxy-5a,6-anhydrotetracycline into 7-chloro-5a,6-anhydrotetracycline was successfully carried out.
In a different approach it was attempted to convert the synthetic tetracycline derivative 7-chloro-4-dedimethylamino-5a,6-anhydrotetracycline to 7-chloro-5a,6-anhydrotetracycline via a series of bromination-aminatipn experiments. Chromatographic evidence is presented for the formation, in trace amounts, of 7-chloro-5a,6-anhydro-4-epi-tetracycline.
Part II is concerned with the study of the possible precursor activity of triacetic acid lactone, a potential polyketomethylene chain intermediate in the biosynthesis of aromatic compounds. (3,5-¹⁴ C) Triacetic acid lactone was fed to P. patulum and labelled griseofulvin was isolated and degraded. It was found that radioactivity is incorporated into griseofulvin a non-specific way. In one strain of the mould used two new metabolites were found as a result of the addition of triacetic acid lactone. Addition of triacetic acid lactone to the mould also causes an unexplained enhancement of metabolite formation.
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Genre | |
Type | |
Language |
eng
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Date Available |
2011-09-29
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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 |
10.14288/1.0062191
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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 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.