Precursor-directed biosynthesis of non-natural berberine and galanthamine analogues

<p> Precursor-directed biosynthesis and mutasynthesis are two methods which utilize nature’s machinery to produce complex natural product analogues. The berbine-producing <em>Berberis Stenophyllia</em> 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 <em>Berberis Stenophyllia</em> and daffodils to produce fluorinated berberine and galanthamine analogues.</p>

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2011

Author dc:creator

• Speltz, Tom E

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

Repository record dc:identifier

https://via.library.depaul.edu/etd/91

OAI identifier oai:identifier

oai:via.library.depaul.edu:etd-1092