Date of Award


Document Type


Degree Name

Doctor of Philosophy (PhD)



First Advisor

Matthias Brewer

Second Advisor

Christopher Franckyln


This dissertation describes research into the synthesis of carbon nanotubes using traditional organic synthetic methods, as well as work on the fragmentation of β-hydroxy-α-diazoesters with a γ-hetero group and applications of their reactivity towards natural product synthesis.

Carbon nanotubes are unique structures that can exhibit different electronic properties based on their chiral vector, and are a potential future source of semiconductors. Current methods of synthesis are unable to be adapted to commercial synthesis, providing the opportunity for the application of organic synthetic methods to generate them more uniformly and on a larger scale.

The generation of tethered aldehyde ynoates and their utilization in 1,3-dipolar cycloadditions has been well developed by the Brewer group. Traditionally they have been generated from γ-siloxy-β-hydroxy-α-diazoesters, herein we explore utilizing an amino group as the fragmentation initializer. Additionally, application of the tethered aldehyde ynoate towards the synthesis of the natural products Demissidine and Aspidospermine are discussed.



Number of Pages

182 p.