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
Copyright Date
2016
Language
en
File Format
application/pdf
File Size
133 pages
Recommended Citation
Wanninayake, Umayangani Kumari, "Understanding the reactivity of triacetic acid lactone" (2016). Graduate Theses and Dissertations. 15836.
https://lib.dr.iastate.edu/etd/15836
