| dc.description.abstract | Avenanthramides (AVAs) are a group of phenolic compounds that can be found in oat (Avena Sativa) and act as defence mechanism against several pathogens. Avenanthramides (AVAs) are responsible for some health benefits in oat such as antioxidant and anti-inflammatory. The aim in this thesis is to synthesize one avenanthramide called Avenalumamide AF8. Several synthetic methods were explored in the synthesis toward Avenalumamide AF8.
In the synthesis of Avenalumamide AF8, the focus was to synthesize the biggest unit of the compound and this unit of is an avenalumic acid moiety. Potassium (1E,3E)-5-oxopenta-1,3-dien-1-olate was synthesized with great yields in a pyridinium anion ring-opening reaction and served as a starting material in subsequent reactions towards the synthesis of the avenalumic acid moiety. The starting material was used with a Grignard reagent in an attempted synthesis of (2E,4E)-5-(4-hydroxyphenyl) penta-2,4-dienal. This compound was later synthesized with an organolithium instead of a Grignard reagent, but the result was a product with low yield. The synthesis attempt of methyl (2E,4E)-5-bromopenta-2,4-dienaote was another approach towards the synthesis of the avenalumic acid moiety.
The synthesis towards Avenalumamide AF8 was not completed because of the limited time frame for this master thesis. With more time, some of these reactions would have been optimized and the synthesis of the anthranilic acid moity of Avenlumamide AF8 would have been explored. | |
