Part I. The Isolation and Structure of Two Alkaloids from Tabemaemontana rupicola. Part II. The Structure of Necrosamine

Citation

Kessel, James W. (1963) Part I. The Isolation and Structure of Two Alkaloids from Tabemaemontana rupicola. Part II. The Structure of Necrosamine. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/CRDM-RN71. https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899

Abstract

Part I

Two alkaloids have been isolated from the leaves and twigs of Tabernaemontana rupicola, a South American shrub. Physical and chemical data indicate that one of these alkaloids, named rupicoline, is 18–carbomethoxyiboluteine, a pseudoindoxyl compound closely related to the alkaloid voacangine. The second alkaloid, named montanine, is believed to be 18-carbomethoxy-20-hydroxyiboluteine. However, attempts to prove this structure for montanine by converting some of this alkaloid to rupicoline were unsuccessful. Experiments were also conducted which suggest that these alkaloids are not artifacts of the isolation procedure.

Part II

Necrosamine, a base isolated from an Escherichia coli lipopolysaccharide causing the regression of an experimental mouse tumor, yields, when oxidized with periodate and permanganate, n-butyric acid. Necrosamine is therefore an isomer of 4, 5-diaminoeicosane. Several attempts were made to resolve synthetic 4, 5-diaminoeicosane. These were unsuccessful as were attempts to prepare a derivative of necrosamine with a detectable optical rotation.

Thesis Files