Model Studies Toward the Total Synthesis of Lycolucine and the Development of Various Synthetic Methods

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dc.contributor.advisor Prof. Jonathan S. Lindsey, Committee Member en_US
dc.contributor.advisor Prof. Paul A. Maggard, Committee Member en_US
dc.contributor.advisor Prof. Daniel L. Comins, Committee Chair en_US
dc.contributor.advisor Prof. Suzanne T. Purrington, Committee Member en_US
dc.contributor.author Dinsmore, Jason Matthew en_US
dc.date.accessioned 2010-04-02T19:15:19Z
dc.date.available 2010-04-02T19:15:19Z
dc.date.issued 2007-04-19 en_US
dc.identifier.other etd-04032007-223017 en_US
dc.identifier.uri http://www.lib.ncsu.edu/resolver/1840.16/5527
dc.description.abstract A study directed at the total synthesis of lycolucine was carried out and discussed within. Various synthetic routes were attempted toward this end. The synthetic schemes all revolve around utilization of the well-established N-acylpyridinium salt chemistry as the foundational method of synthesis. One approach employs metathesis chemistry to attempt the construction of a key carbon-carbon bond. The development of a one-pot alkene homologation was discovered. This investigation reveals the ability to homologate terminal alkenes by one carbon utilizing the 2nd generation Grubbs catalyst. Various aromatic and non-aromatic substrates were used to demonstrate the scope of the reaction, with yields ranging from 65% to 86%. This work reveals the first example of a one-pot one carbon alkene homologation from an existing terminal alkene. A few synthetic methods, such as the formation of indolizidine scaffolds and amino alcohols, are also discussed. Various compounds were realized that could potentially lead to the development of more complex structures. en_US
dc.rights I hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dis sertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to NC State University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report. en_US
dc.subject lycolucine en_US
dc.subject synthesis en_US
dc.subject terminal alkenes en_US
dc.subject indolizidine en_US
dc.title Model Studies Toward the Total Synthesis of Lycolucine and the Development of Various Synthetic Methods en_US
dc.degree.name PhD en_US
dc.degree.level dissertation en_US
dc.degree.discipline Chemistry en_US


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