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

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.

Identiferoai:union.ndltd.org:arizona.edu/oai:arizona.openrepository.com:10150/184620
Date January 1988
CreatorsKilama, John Jolly.
PublisherThe University of Arizona.
Source SetsUniversity of Arizona
LanguageEnglish
Detected LanguageEnglish
Typetext, Dissertation-Reproduction (electronic)
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.

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