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
Copyright Date
2003
Language
en
Proquest ID
AAI3143529
File Format
application/pdf
File Size
155 pages
Recommended Citation
Kim, Ikyon, "Direct approaches to natural product synthesis " (2003). Retrospective Theses and Dissertations. 918.
https://lib.dr.iastate.edu/rtd/918
