I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine

<p>Part I</p> <p>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 rela...

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Main Author: Kessel, James W.
Format: Others
Published: 1963
Online Access:https://thesis.library.caltech.edu/6964/1/Kessel_jw_1963.pdf
Kessel, James W. (1963) I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/CRDM-RN71. https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899 <https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899>
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spelling ndltd-CALTECH-oai-thesis.library.caltech.edu-69642019-12-22T03:09:29Z I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine Kessel, James W. <p>Part I</p> <p>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.</p> <p>Part II</p> <p>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.</p> 1963 Thesis NonPeerReviewed application/pdf https://thesis.library.caltech.edu/6964/1/Kessel_jw_1963.pdf https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899 Kessel, James W. (1963) I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/CRDM-RN71. https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899 <https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899> https://thesis.library.caltech.edu/6964/
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format Others
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description <p>Part I</p> <p>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.</p> <p>Part II</p> <p>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.</p>
author Kessel, James W.
spellingShingle Kessel, James W.
I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine
author_facet Kessel, James W.
author_sort Kessel, James W.
title I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine
title_short I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine
title_full I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine
title_fullStr I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine
title_full_unstemmed I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine
title_sort i. the isolation and structure of two alkaloids from tabernaemontana rupicola. ii. the structure of necrosamine
publishDate 1963
url https://thesis.library.caltech.edu/6964/1/Kessel_jw_1963.pdf
Kessel, James W. (1963) I. The isolation and structure of two alkaloids from Tabernaemontana rupicola. II. The structure of necrosamine. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/CRDM-RN71. https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899 <https://resolver.caltech.edu/CaltechTHESIS:04242012-131610899>
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