27478 - Planning organic syntheses

Learning outcomes

The student is able to plan alternative synthetic approaches of an organic molecule accoridng to the retrosynthetic analysis and is able to compare different routes on the basis of economy, sustainability and practicality.

Course contents

Cntents: 1) Retrosynthesis, concepts and terms. Identification of disconections. Guidelines to the identification of useful disconnections and their comparison. Umpolung synthons. 2) Functional Group Interconversions. 3) Retrosynthesis of alkanes, alkenes and alkynes. 4) Retrosynthesis of monofunctional molecules: Disconnection-key reaction correlation tables. 5) Retrosynthesis of bifunctional molecules: functionality span-key reaction correlation tables. 6) Retrosynthesis of cyclic molecules: Anellation, cyclization and reconnection reactions. 7) Main strategies to the synthesis of asymmetric molecules.

Readings/Bibliography

Worksheet and tutorials provided by the professor are essential.

For an in-depth study of organic synthetic design see:

·        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

Classic lessons are followed by exercises on the application of retrosynthetic analysis to the design of multistep syntheses.

Assessment methods

A preliminary written test open the access to the oral examination where a given molecule is to be retrosynthetically analyzed in order to propose different synthetic routes.

Teaching tools

Overhead projector, PC

Office hours

See the website of Claudio Trombini

See the website of Marco Lombardo