Advanced Topics in Organic synthesis
Theory: 2 hours/week | Practicals: 3 hours/week | ECTS Units: 4
Tutoring in the English language is offered to Erasmus students
Learning outcomes
The aim of the course is to provide students with deeper knowledge of the methodology and techniques of Organic Synthesis, with emphasis on their practical application in the synthesis of biologically important compounds.
Upon completion of the course, students are expected to be able to:
- select appropriate methods for the stereoselective synthesis of compounds with double bonds,
- design and execute synthetic routes to produce peptides, through sequential steps of protection, coupling and deprotection,
- perform glycosylation reactions for the synthesis of nucleosides,
- recognize important classes of heterocyclic compounds and apply known methods for the synthesis of representative members of each class.
Syllabus
- Advanced laboratory techniques: purification and drying of solvents, handling of reagents sensitive to moisture or atmospheric oxygen, reactions under inert conditions, heating using microwaves, isolation and purification of products (extraction, distillation, recrystallization, column chromatography).
- Design of routes for the synthesis design of complex organic compounds: literature search, organic synthesis strategies, retrosynthetic analysis, use of amino acids and sugars as starting materials, utilization of stereoselective reactions.
- Structure identification: determination of melting point of solid compounds, spectroscopic techniques: infrared (IR), ultraviolet (UV), nuclear magnetic resonance (NMR) and mass (MS).
- Application of organic reactions: introduction and removal of protecting groups, oxidation and reduction, formation of double bonds (Wittig and Horner-Wadsworth-Emmons reactions), coupling reactions with palladium catalysts, 1,3-dipolar cycloadditions, multicomponent reactions (MCR).
- Synthesis of compounds of biological interest: coupling of nitrogenous bases and sugars to produce nucleosides, synthesis of heterocyclic compounds (pyrrole, triazole, quinoline, quinazoline and isoquinoline derivatives).
Student performance evaluation
Students are evaluated based on: a) their performance in the application of experimental techniques and the execution of synthetic procedures, and b) the presentation of a project.
Suggested bibliography
- Organic Chemistry, G. Wade, 9th edition, Pearson, 2024.
- Organic Chemistry, John Mc Murry, 9th edition, Cengage Learning, 2015.
- March’s Advanced Organic Chemistry, M. B. Smith, J. March, Wiley-Interscience, 5th Edition.
- Experimental Organic Chemistry, L. M. Harwood, C. J. Moody, Blackwell Scientific Publications.
- Protective Groups in Organic Synthesis, T. W. Greene, P. G. M. Wuts, Wiley-Interscience; 3rd Edition.
Teaching Material / E-class
Lecturers
