Degree Type

Dissertation

Date of Award

2006

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

George A. Kraus

Abstract

In this dissertation, we have investigated the direct and efficient synthetic route to biologically active natural products;Chapter 1 describes a concise and efficient synthetic route to the highly funtionalized tricyclic core skeleton of papuaforin B. In the course of the synthesis, an efficient cyclization method using Na/NH3 was demonstrated. Newly developed bromination method leading to an alpha-bromoenone would serve as a handle for construction of the fused pyran ring of papuaforin B. Further efforts along this line are in progress;Chapter 2 describes the direct synthesis of 7,8-dihydroxycalamenene, which includes the successful application of allylic strain in the stereoselective synthesis. Interestingly, Mansonone C, a potent antifungal agent, was also obtained as the co-product from the same starting material. Application of this synthetic strategy to the synthesis of analog natural products is in progress.

DOI

https://doi.org/10.31274/rtd-180813-16461

Publisher

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

Copyright Owner

Insik Jeon

Language

en

Proquest ID

AAI3243830

File Format

application/pdf

File Size

118 pages

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