Date of Award
Fall 12-2014
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.
Recommended Citation
Thota, Kiran Kumar, "Studies Directed Toward the Synthesis of Amphibian Alkaloids via Iridium Catalyzed N-Heterocyclization Reactions" (2014). University of New Orleans Theses and Dissertations. 1950.
https://scholarworks.uno.edu/td/1950
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.