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. http://resolver.caltech.edu/CaltechETD:etd-10092002-153828
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.
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.
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.))|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||1 January 1964|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Imported from ETD-db|
|Deposited On:||10 Oct 2002|
|Last Modified:||26 Dec 2012 03:04|
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