A new synthetic approach to the C-D ring portion of streptonigrin and its analogs.

Persistent Link:
http://hdl.handle.net/10150/184620
Title:
A new synthetic approach to the C-D ring portion of streptonigrin and its analogs.
Author:
Kilama, John Jolly.
Issue Date:
1988
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Two new synthetic methods for the construction of the C-D moiety of streptonigrin have been developed. The first is the cyclization of beta, gamma unsaturated ketals to cyanopyridines. These ketals were prepared from akylidenemalononitriles. The second method utilized is the ortho-directed metalation of benzamide or oxazoline derivative to give keto compounds. However, attempts to transform these keto compounds to akylidenemalononitriles by Knoevenagel condensations were unsuccessful. With the ease of the reaction and ready availability of starting materials, the beta, gamma unsaturated ketals offer versatile synthons for pyridine C ring synthesis.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Antineoplastic agents -- Synthesis.; Natural products -- Synthesis.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Pharmaceutical Sciences; Graduate College
Degree Grantor:
University of Arizona

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleA new synthetic approach to the C-D ring portion of streptonigrin and its analogs.en_US
dc.creatorKilama, John Jolly.en_US
dc.contributor.authorKilama, John Jolly.en_US
dc.date.issued1988en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractTwo new synthetic methods for the construction of the C-D moiety of streptonigrin have been developed. The first is the cyclization of beta, gamma unsaturated ketals to cyanopyridines. These ketals were prepared from akylidenemalononitriles. The second method utilized is the ortho-directed metalation of benzamide or oxazoline derivative to give keto compounds. However, attempts to transform these keto compounds to akylidenemalononitriles by Knoevenagel condensations were unsuccessful. With the ease of the reaction and ready availability of starting materials, the beta, gamma unsaturated ketals offer versatile synthons for pyridine C ring synthesis.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectAntineoplastic agents -- Synthesis.en_US
dc.subjectNatural products -- Synthesis.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplinePharmaceutical Sciencesen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.identifier.proquest8907964en_US
dc.identifier.oclc701917228en_US
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