Citation
Olson, Edwin Soland (1964) The structure of the orange pigment from Pseudomonas aureofaciens. The biogenesis of strychnine. Beckman fission of a gamma-keto oxime. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/V3CJ-7176. https://resolver.caltech.edu/CaltechETD:etd-10092002-153828
Abstract
PART I.
The structure of the orange pigment from Pseudomonas aureofaciens was investigated and found to be 1-carboxy-2-hydroxyphenazine. A degradation product, 1-methyl-2-methoxyphenazine, was shown to be identical to a synthetic sample.
PART II.
The biogenesis of the indole alkaloid, strychnine, was studied by administration of C[superscript 14] labelled precursors to Strychnos nus-vomica plants and degradations of the radioactive strychnine isolated from the plants. The results indicate an acetate origin for the non-tryptophan portion and a formate origin for the "berberine bridge" carbon of strychnine.
PART III.
A Beckmann fission of the tosylate of the [gamma]-keto oxime, 3-acetoxylanostane-7, 11-dione-7-oxime, was carried out with sodium t-butoxide, and the expected cleavage of ring B and formation of a nitrile and unsaturated ketone occurred.
Item Type: | Thesis (Dissertation (Ph.D.)) |
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Degree Grantor: | California Institute of Technology |
Division: | Chemistry and Chemical Engineering |
Major Option: | Chemistry |
Thesis Availability: | Public (worldwide access) |
Research Advisor(s): |
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Thesis Committee: |
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Defense Date: | 1 January 1964 |
Record Number: | CaltechETD:etd-10092002-153828 |
Persistent URL: | https://resolver.caltech.edu/CaltechETD:etd-10092002-153828 |
DOI: | 10.7907/V3CJ-7176 |
Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. |
ID Code: | 3988 |
Collection: | CaltechTHESIS |
Deposited By: | Imported from ETD-db |
Deposited On: | 10 Oct 2002 |
Last Modified: | 20 Dec 2019 19:45 |
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