The course prepares the students in planning Organic Synthesis, defining tactics, strategies with the control of reaction stereochemistry. The final aim is the critical reading and evaluation of the recent literature in the field.
Course Prerequisites
Fundamentals of organic chemistry: The reactivity of Functional groups. Enolate reactivity. Properties and reactivity of mono-, oligo-saccharides and amino acids.
Teaching Methods
Lectures with background information, guidelines and problem solving applied to the retrosynthetic analysis. Flipper classroom strategy. Working students (or equivalent certified conditions, according to the University lecturing guide lines) are supported on request by additional teaching material, including video recordings and two hours per week of dedicated tutorials
Assessment Methods
The oral exam aims to evaluate: 1) the ability of the student to suggest and describe effective synthetic strategies and synthetic routes for organic compounds, with emphasis for commercial drugs, making used of the Retrosynthetic Analysis; 2) the understanding of current literature on organic chemistry, describing the approach adopted in recent papers focused on the stereo-selective generation of new carbon-carbon bonds.
Texts
1. S. Warren, P. Wyatt, “Organic Synthesis: The Disconnection Approach”, 2nd ed., Wiley, 2009; ISBN-13: 978-0470712368 2. S. Warren, P. Wyatt, “Workbook for Organic Synthesis”: The Disconnection Approach, 2nd Edition. ISBN-13: 978-0470712269 3. L. Kürti, B. Czakó, “Strategic Applications of Named Reactions in Organic Synthesis”, Academic Press - Elsevier, 2005; ISBN-13: 978-0124297852 4. W. Carruthers, I. Coldham, “Modern Methods of Organic Synthesis”, 4th ed., Cambridge University Press, 2004; ISBN-13: 978-0511811494 5. R. W. Hoffmann. Elements of Synthesis Planning, Springer 2009; ISBN-13: 978-3540792192
Contents
Basic principles of retrosynthetic analysis. C-C bond (single, double and triple) disconnections, synthons and main transforms (Diels-Alder reactions, sigmatropic [3,3], olefination, click chemistry) to efficiently achieve the synthesis of a target molecule. Organometallics in synthesis (organoboranes, organosilanes, organoalluminiums, Pd-mediated cross-coupling reactions and olefin metathesis). Modern synthetic methods for peptides, saccharides and nucleic acids. Bioorthogonal Chemistry.
Course Language
Italian
More information
Documents (in English) and files shown and described during the 2023 lecturing activity are available in a shared google drive folder. Lecture Podcasts of the year 2021)are available on request.
