Advanced Topics in Organic synthesis
Theory: 2 hours/week | Practicals: 3 hours/week | ECTS Units: 4
Content – Aim of the course
Aim of the course is to provide the students with an advanced knowledge of the methodology and techniques of Organic Synthesis, giving emphasis on their practical application in the synthesis of bioactive compounds.
Analytical Description of the Course
Advanced laboratory techniques: purification and drying of solvents, handling of moisture- or air-sensitive reagents, reactions under inert conditions, microwave heating, isolation and purification of products (extraction, distillation, recrystallization, column chromatography).
Designing routes for the synthesis of complex molecules: literature search, strategies of organic synthesis, retrosynthetic analysis, aminoacids and carbohydrates as synthons, utilization of stereoselective reactions.
Structure elucidation of products: determination of the melting point of solid products, spectroscopic techniques: infrared (IR), ultraviolet (UV), nuclear magnetic resonance (NMR) and mass spectrometry (MS).
Application of specialized organic reactions: introduction and removal of protective groups, oxidation and reduction, double bond formation (Wittig and Horner-Wadsworth-Emmons reactions), palladium catalyzed couplings, 1,3-dipolar cycloadditions, multi-component reactions (MCR).
Synthesis of compounds of biological importance: coupling of nitrogen bases and carbohydrates for the production of nucleosides, synthesis of heterocyclic compounds (pyrrole, triazole, quinoline, quinazoline and isoquinoline derivatives).
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.
Reading Suggestions
- Organic Chemistry, L. G. Wade, Jr., Tziola Publications, 9th Edition.
- Organic Chemistry, John Mc Murry, University of Crete.
- 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
Dimitrios Komiotis (Course Coordinator)
