66214 - Organic Sythesis

Learning outcomes

The student will be able to plan alternative synthetic pathways of an organic molecules by applying the retrosynthetic logic and to compare alternative plans on the basis of economy, sustainability and practicality concepts. The student aquires comnpetence and practical skills on the most frequently used experimental procedures in the multistep synthesis of complex organic molecules.

Course contents

The contents will be as follows: 1. Retrosynthesis. Importance of synthesis. Concepts and terminology of retrosynthetic analysis. Identification of disconnections. Guidelines for choosing disconnections and evaluating routes. Reversed polarity synthons. 2. Functional Group Interconversion Reactions. 3. Retrosynthesis of alkanes, alkenes and alkynes. 4. Retrosynthesis of Monofunctional Target Molecules. Functional group/disconnection/key reaction correlation tables. 5. Retrosynthesis of Difunctional Targets. Functional group span/disconnection/key reaction correlation tables. 6. Retrosynthesis of cyclic target molecules. Annellation, cyclization, reconnection routes. 7. Protection of functional groups.     8. Redox reactions.

Readings/Bibliography

Handouts provided by the teaching staff and lecture notes will be essential.

Further readings:

·        K. C. Nicolaou, E. J. Jorgensen, “Classics in Total Synthesis”, VCH.

·        K. C. Nicolaou, S. A. Snyder, “Classics in Total Synthesis II”, Wiley-VCH.

·        M. B. Smith, “Organic Synthesis”, McGraw Hills-Chemistry Book.

·        S. Warren, "Organic Synthesis: The Disconnection Approach", Wiley.

·        P. Wyatt, S. Warren, "Organic Synthesis: Strategy and Control (5)", Wiley.

·        C. Willis, M. Wills, "Organic Synthesis", Oxford Chemistry Primers N. 31.

·        G.D. Meakins, "Functional Groups: Characteristics and Interconversions", Oxford Chemistry Primers N. 35.

Teaching methods

Each lesson will be integrated by exercises in order to train students in using the retrosynthetic approach to problem solving in devising multistep syntheses of a target molecule.

Assessment methods

A written text must be passed to be admitted to the oral exam. The written text is centered on the experimental work done and includes excercises on synthetic techniques. The oral examination will be based on the retrosynthetic analysis of an assigned target molecule, on the identification of a few alternative syntheses and in their comparison in terms of economy, sustainability and practicality.

Teaching tools

PC, video-projector, overhead projector

Office hours

See the website of Claudio Trombini

See the website of Marco Lombardo