Date of Award

Summer 8-4-2011

Degree Type

Dissertation-Restricted

Degree Name

Ph.D.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Jursic, Branko S.

Second Advisor

Trudell, Mark L.

Third Advisor

Cole, Richard

Fourth Advisor

Morgan, Lee Roy

Fifth Advisor

Sakaranarayanan, Ananthakrishnan

Abstract

Magnesidin is a magnesium chelate of the 3-hexanoyl and 3-octanoyl tetramic acid derivatives isolated from Psuedomonas magensiorubra. Its activity against grampositive bacteria was found to be a specific target for Gingivitis, a dental plaque.Although the synthesis of magnesidin has been reported earlier, it was not reproducible. The highly polar nature and it’s ability to exhibit tautomerization makes their chemical behavior complex and difficult to predict its structure. A variety of reactions and an in depth understanding of the chemical structure is necessary to attain the synthesis of these compounds. This dissertation focuses on addressing the attempts towards the synthesis of Magnesidin by identifying the important intermediates necessary for the synthesis as β- keto esters, α,β-unsaturated amino esters. The focus of the work has been addressed by developing a TAG molecule approach, which is similar to the concept of solid phase synthesis except for the fact that the TAG molecule can be identified under UV and also can be detected using various spectroscopic techniques. Microwave synthesis has been explored and applied in to the synthesis of benzyl mono and di bromination, 1,3- benzodioxoles have been established. The benzyl mono bromination is applied to synthesize the TAG molecule, which is then applied in developing a method of synthesis for β-keto esters. The azide approach was used to synthesize the α,β- unsaturated amides, which are another essential class of compounds in the synthesis of magnesidin.

Rights

The University of New Orleans and its agents retain the non-exclusive license to archive and make accessible this dissertation or thesis in whole or part in all forms of media, now or hereafter known. The author retains all other ownership rights to the copyright of the thesis or dissertation.

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Chemistry Commons

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