Degree Type

Dissertation

Date of Award

2016

Degree Name

Doctor of Philosophy

Department

Chemistry

Major

Organic Chemistry

First Advisor

George A. Kraus

Second Advisor

Brent H. Shanks

Abstract

The chemical industry has been dependent on petroleum-derived carbon for commodity chemicals for the past number of decades, but this practice is not sustainable. With the increase of energy demand, biomass has attracted attention for being an inexpensive renewable carbon source. The proposed platform chemical, triacetic acid lactone, can be produced by microbes from glucose. Triacetic acid lactone can subsequently be converted into a multitude of high-value added bio based chemicals via further chemical transformations.

In this dissertation, we explore methods to functionalize triacetic acid lactone to obtain biologically important specialty molecules from biorenewable sources. Chapter 1 of the dissertation describes the synthesis of high value added specialty chemical, pogostone and its analogs from biobased triacetic acid lactone. These high value specialty chemicals are synthesized in high yields and the biological activities are investigated. Chapter 2 discusses an improved aldol protocol for the synthesis of 6-styrenylpyrones from triacetic acid lactone. Styrenyl pyrones are an emerging class of natural products, which exhibit several biological activities. This aldol condensation reaction proceeds in good yields and is compatible with a variety of functional groups. Chapter 3 describes the use of triacetic acid lactone as a common intermediate for the synthesis of 4-hydroxy-2-pyridones and 4-amino-2-pyrones. As demonstrated therein, triacetic acid lactone constitutes a useful platform for the direct introduction of a nitrogen functionality. In summary, triacetic acid lactone represents a convenient biobased platform for a diverse range of important molecules.

DOI

https://doi.org/10.31274/etd-180810-5463

Copyright Owner

Umayangani Kumari Wanninayake

Language

en

File Format

application/pdf

File Size

133 pages

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