Degree Type

Dissertation

Date of Award

2003

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

George A. Kraus

Abstract

In this dissertation, we have investigated direct routes to several biologically important natural products.;Chapter 1 describes a concise construction of core skeleton of malibatol A, employing a novel benzofuran formation methodology and a regio- and stereoselective 7-membered ring formation via Lewis acid catalyzed epoxide ring opening as crucial steps.;Chapter 2 describes direct approaches to isoflavanquinones utilizing radical addition to quinones. Three main strategies were presented and were compared to generate radicals from the corresponding precursors.;Chapter 3 describes a direct entry to erogorgiaene, naturally occurring potent antitubercular agent, featuring a regioselective metal-halogen exchange and a 6-exo-trig radical cyclization as key transformations.;Chapter 4 describes synthetic studies towards antitubercular benzoxazole alkaloids. The core tricyclic skeleton of the originally proposed structures of these natural products was synthesized using an intermolecular Diels-Alder reaction as a key step.

DOI

https://doi.org/10.31274/rtd-180813-10941

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu

Copyright Owner

Ikyon Kim

Language

en

Proquest ID

AAI3143529

File Format

application/pdf

File Size

155 pages

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