Concepts and Methods in Organic Synthesis

Goals
The purpose of this course is to furnish to chemistry students, interested in deepening organic synthesis, methods and tools for organizing and rationalizing all their organic chemistry knowledge, acquired in previous organic chemistry courses. In particular, the course will focus on the following aspects: concepts, methods and reagents useful for the design of organic systems, taking into account, in particular, methods to achieve reaction selectivity and commercially availability of starting reagents.

Acquired skills
At the end of the course, the student will be able to face the issue of planning a synthetic procedure for marketable organic compounds.

Course content
The course illustrates in detail three fundamental aspects related to the learning of how to design the synthesis of organic molecules: 1] concepts, 2] synthetic methods, and 3] reagents, earlier in the process of the synthesis of an organic molecule.
1. Concepts include: the regio- and stereoselective formation of C-C bonds; transformation and protection of functional groups. Strategies to promote thermodinamically unfavourable reactions.
2. Synthetic methods are discussed in terms of: applicability; simplicity; selectivity.
3. Reagents include: how to make the choice of starting materials for an organic synthesis, on the base of costs, safety, and commercial availability.
The concept of synthon is defined and illustrated in detail, as well as its use in the design of organic molecules.
The retrosynthetic analysis is described as a fundamental tool for the organic synthesis. Organic compounds are classified on the basis of the distance of functional groups and retrosynthetic methodologies for their preparation, considering stereo- and regioselective aspects, are explained.
Coupling reactions mediated by boranes, cuprates and transition metals are also described. A review of the main methods of oxidation and reduction of organic compounds are listed.
At the end of the course, several examples of retrosynthetic analysis, as exercises, are discussed.
The course is implemented with one or two seminars given by experts involved in the industrial production of active principal ingredients.

Suggested prerequisites
Courses of Organic Chemistry I and II

Reference material
a) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, V Edition, 2007 Springer Science.
b) J. Clayden, N. Greeves, S. Warren - Organic Chemistry, II Edition, 2012 Oxford
c) S. Warren, P. Wyatt - Organic Synthesis: The Disconnection approach. 2008 Wiley
d) S. Warren, P. Wyatt - Workbook for Organic Synthesis: The Disconnection approach. II Edition, 2008 Wiley

Prerequisites
Basic concepts of organic chemistry. Standard techniques for purification and structure elucidation (NMR, MS, IR).

Assessment method
Written examination. The written exam is usually composed by 6-8 exercises related to the synthesis of organic molecules.

Language of instruction
English

Attendance Policy:
Recommended.

Mode of teaching:
traditional

Website
http://ariel.unimi.it/

Further Information
Copies of the lecture slides and other material considered useful for an in-depth study are available on Ariel web page after the end of each lesson.