Date of Award

Fall 12-18-2014

Degree Type

Dissertation

Degree Name

Ph.D.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Trudell, Mark

Second Advisor

Jursic, Branko

Third Advisor

Wiley, John

Fourth Advisor

Rick, Steven

Abstract

The pyrrolidine and piperidine ring systems are present in a variety of different classes of amphibian alkaloids. We have found the iridium catalyzed N-heterocylization reaction of diols with amines to be very useful for the construction of novel pyrrolidine, piperidine and piperazine derivatives. The scope and utility of the iridium catalyzed N-heterocyclization reaction for the construction of novel anuran scaffolds using amino diols and triols are presented. Studies directed towards the total synthesis of 4,6-disubstituted quinolizidine and (±)-epiquinamide are discussed.

The second study is focused on the selective conversion of terminal dienes to primary diols. This conversion has always had problems with regioselectivity and low yields due to polymer formation with carbon chains having more than 7 carbon atoms. An improvement in the yield and regioselectivity was observed with disiamylborane prepared in situ using 2-methyl-2-butene and BH3•DMS. The scope of this method with 7, 8 and 9 carbon chains and different alcohol protecting groups for synthesis of triols is presented.

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 in 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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