Today, october 24rd, the CIQUS PhD student Marcos Alejandro González Castro obtained the maximum qualification for the defense of his Doctoral Thesis entitled "New synthetic applications of D-glucose and (-)-shikimic acid: synthesis of polyhydroxylated derivatives of 2-(2- aminocyclohexyl)acetic acids, 2-aminomethylcyclohexancarboxilic acids, azepanes and cyclohexan-1,2-dimines". His work has been supervised by Professors Ramón José Estévez Cabanas and. Juan Carlos Estévez Cabanas.
Natural products are useful starting materials for the synthesis of new molecules with potential applications in materials science and pharmacology. These include D-glucose, a very cheap and abundant monosaccharide, which, despite being widely used in organic synthesis, offers possibilities not yet explored, some of which are studied in this thesis. Another natural product is (-)-shikimic acid, whose recent synthetic interest is related to its use as starting material for the synthesis of potent influenza drug oseltamivir (Tamiflu®), a reference drug to the treatment of the avian flu.
This thesis addresses the development of the synthesis of ϒ-amino acids from D-glucose-based nitrosugars and from (-)-shikimic, mainly polyhydroxylated cyclohexane ϒ-amino acids. Additional synthetic possibilities offered both starting materials have been explored, including studies on new iminosugars, new cyclohexane-1,2- diamine organocatalysts and the aliphatic component of the HIV integrase inhibitor included in this abstract.
