I. The Structure of the Orange Pigment from Pseudomonas aureofaciens. II. The Biogenesis of Strychnine. III. Beckmann Fission of a γ-Keto Oxime

Citation

Olson, Edwin Soland (1964) I. The Structure of the Orange Pigment from Pseudomonas aureofaciens. II. The Biogenesis of Strychnine. III. Beckmann Fission of a γ-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.

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