Degree Type

Dissertation

Date of Award

2000

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

George A. Kraus

Abstract

Organic synthesis is a highly-developed, useful, and interdisciplinary branch of natural science. Modern synthetic chemistry has provided complex molecules and new materials with unique properties. This study focused on creating new methodology, or new routes, to achieve a biologically active, natural product synthesis;A new methodology to generate 2,4-diacylfuran compounds has been developed and discussed. The synthesis of two natural 2,4-diacylfuran compounds, hibiscone C, and halenaquinone, has been achieved. The new route to hibiscone C features an efficient ring formation and rearrangement. Halenaquinone analogues have been synthesized by Michael addition, annulation, and palladium catalyzed reaction. The new route provides a new lead in the discovery of anticancer reagents like halenaquinone;A first approach towards building a BCD ring system for aquayamycin via intramolecular anion reaction is described. The approach could eventually provide a route to achieve the total synthesis of aquayamycin, a new antibiotic which might eventually be used to treat cancer.

DOI

https://doi.org/10.31274/rtd-180813-15290

Publisher

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

Copyright Owner

Zhiwen Wan

Language

en

Proquest ID

AAI9962854

File Format

application/pdf

File Size

83 pages

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