Date of Award

5-19-2015

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Department of Chemistry

First Advisor

Timothy A. Mitchell

Abstract

Oxidopyrylium-based [5+2] cycloadditions have been extensively utilized to construct oxabridged seven-membered ring systems that often serve as the core structures in numerous biologically active natural products. By investigating these processes, we hope to reveal the highest potentials of [5+2] cycloaddition as a synthetic tool.

A novel oxidopyrylium-alkene [5+2] cycloaddition conjugate addition cascade (C3) sequence, which allows rapid build-up of molecular complexity with excellent diastereocontrol, was investigated. The scope and limitation of this process were explored as mixed results were shown for various acetoxypyranone-alkene substrates. In addition, oxidopyrylium [5+2] cycloadditions of ï?¢-silyloxy-ï?§-pyrones were investigated which revealed the accelerating role of carbonyl substituents at the trans-terminal position of alkenes. Finally, we have demonstrated the utility of sulfinimine chiral auxiliary in the asymmetric [5+2] cycloaddition of ï?¢-silyloxy-ï?§-pyrones.

Comments

Imported from ProQuest Law_ilstu_0092N_10549.pdf

DOI

http://doi.org/10.30707/ETD2015.Law.C

Page Count

196

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Available for download on Monday, January 19, 2026

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