Supervisors info:
Γεώργιος Κόκοτος, Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Summary:
An important objective of organic synthesis is the formation of optically active compounds, which can be used as synthetic intermediates for a variety of organic transformations. Epoxide rings constitute such intermediates as they participate in various stereospecific reactions. As a result of the above, the development of methods for asymmetric synthesis of epoxides, which can be used either as key intermediates in the preparation of more complex optically pure bioactive compounds or as final products also exhibiting biological activities, has attracted the interest of the scientific community.
In the present work, asymmetric synthesis of saturated hydroxy fatty acids was achieved, in which the formation of asymmetric epoxide using organocatalysts was the key step for the introduction of chirality. Saturated hydroxy fatty acids have recently begun to attract the interest of researchers, who focus on their biological role. Specifically, 3-hydroxy fatty acids present more effective binding to free fatty acid receptors, such as GPR84. In addition, optically active β-hydroxy fatty acids are important structural compounds in organic synthesis, for example in the synthesis of β-amino acids, β-lactams and pheromones.
Another class of compounds that has attracted interest is N-protected α-amino epoxides. More specifically, (2S,3S)-3-amino-1,2-epoxy phenylbutane and (2R,3S)-3-amino-1,2-epoxy phenylbutane belong to the class of compounds that serve as intermediates in the preparation of more complex chiral bioactive compounds as they participate in the synthesis of approved inhibitors of HIV protease, Saquinavir, Amprenavir and Atazanavir. In the present thesis we focused on the synthesis of the above diastereomers in their enantiomerically enriched form, using organocatalysts.
