College of Liberal Arts & Social Sciences Theses and Dissertations

Graduation Date

6-2011

Document Type

Thesis

College/Department Conferring Degree

Chemistry

Keywords

precurser-directed biosynthesis, berberine, galanthamine, mutasynthesis, natural product analogues

Abstract

Precursor-directed biosynthesis and mutasynthesis are two methods which utilize nature’s machinery to produce complex natural product analogues. The berbine-producing Berberis Stenophyllia and galanthamine-producing daffodils are chosen as model organisms to evaluate these novel techniques in plants. The synthetic targets chosen as primary precursor analogues to produce fluorinated berberine and galanthamine analogues are 5-fluorodopmaine, 2-fluorodopamine, 3-fluorotyrmaine, and 5-fluoroprotocatechualdehyde. 5-Fluorodopamine is synthesized in 43% yield from 3-fluoroanisole and the crystal structure is reported. Progress towards the synthesis of the three other pre-cursor analogues is reported as well as developing procedures to use Berberis Stenophyllia and daffodils to produce fluorinated berberine and galanthamine analogues.

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