Tesis doctoral de Jordi Aguilera Corrochano
(-)-verbenone has been used as chiral starting material in the synthesis of optically pure compounds which include unnatural ¿-amino acids, ¿-peptides, ¿-lactams, pyrrolidines and related compounds containing a cyclobutane ring in their structure. efficient methodologies for the synthesis of optically active cyclobutyl ¿-lactams and pyrrolidines have been developed. These strategies have as a key synthetic transformation a stereoselective 1,4-conjugate addition of nitromethane to suitable olefins. the synthesis of cyclobutyl pyrrolidines has been carried out using two different routes. The first one requires the reduction of the carbonyl group in optically pure ¿-lactams. The second one is based on a cyclisation of suitable amino alcohols via a mitsunobu reaction. preliminary tests in the application of the newly synthesised cyclobutyl pyrrolidines as stabilizers of transition metal nanoparticles have been performed. It is planned to study in the future not only the formation of new metal nanoclusters but also their characterisation and application as asymmetric catalysts. cyclobutane ¿-peptides with modular constraint have been synthesised with the aim to study their structural properties which could lead to the obtention of new materials. The preliminary studies point out that the cyclobutane moiety disrupts the natural tendency of non-constrained ¿-peptides to form intramolecular hydrogen bonds between the nearest neighbour amide groups on the polymer backbone. These non-covalent interactions are responsible for the no formation of compact folding patterns in most of the studied ¿-peptides.
Datos académicos de la tesis doctoral «Stereoselective synthesis of cyclobutyl gamma-lactams, pyrrolidines and gamma-peptides«
- Título de la tesis: Stereoselective synthesis of cyclobutyl gamma-lactams, pyrrolidines and gamma-peptides
- Autor: Jordi Aguilera Corrochano
- Universidad: Autónoma de barcelona
- Fecha de lectura de la tesis: 20/07/2010
Dirección y tribunal
- Director de la tesis
- Rosa María Ortuño Mingarro
- Tribunal
- Presidente del tribunal: mercedes Amat tusón
- claudia Tomasini (vocal)
- (vocal)
- (vocal)