Learning objectives
1 - KNOWLEDGE AND UNDERSTANDING
At the end of the course, students are expected to have gained the following skills:
1) to explain the basics of stereochemistry and the most useful methods to determine the optical purity of stereoisomers;
2) to explain the main implications between the chirality of a molecule and its bioactivity;
3) to know the main sources of chiral bioactive molecules;
4) to know the basics of asymmetric catalysis: metal-catalysis and organocatalysis;
5) to critically review a synthetic strategy aimed at the preparation of small, chiral, polyfunctionalized molecules.
2 - APPLYING KNOWLEDGE AND UNDERSTANDING
At the end of the course, students are expected to have gained the following skills:
1) to classify molecules according to their stereochemistry;
2) to be able to evaluate diastereomeric and enantiomeric excesses of a given mixture;
3) to be able to describe the main routes for the supply of chiral molecules;
4) to be able to describe the basics of asymmetric catalysis.
3 - MAKING JUDGEMENTS
At the end of the course students are expected to have gained the following skills:
1) to propose a viable methodology to determine the stereoisomeric excesses of a given mixture of stereoisomers;
2) to compare different asymmetric synthesis processes, based on their respective advantages and disadvantages.
4 - COMMUNICATION SKILLS
At the end of the course students are expected to have gained the following skills:
-being able to communicate the results of an empirical research to a non-expert audience;
-being able to draft a formal, orderly, comprehensible document that is appropriate to the professional context;
-knowing how to produce a written work morphologically, syntactically and grammatically correct about a reported stereoselective total synthesis.
5 - LEARNING SKILLS
At the end of the course students are expected to have gained the following skills:
-being able to retrieve and apply new information, compared to that provided during the training, necessary to evaluate and compare the different synthetic approaches of chiral molecules of pharmaceutical interest;
-being able to link the different topics covered with each other and with basic and related disciplines;
-to continuously update through consultation of relevant scientific publications.
Prerequisites
To fully appreciate the content of the course, it is necessary to acquire knowledge of organic chemistry basics as addressed in the previous Organic Chemistry I and II courses.
Course unit content
The issue of drug chirality is now a major theme in the design and development of new drugs, underpinned by a new understanding of the role of molecular recognition in many pharmacologically relevant events. The course will focus on stereoselective synthetic methods and strategies as well as retrosynthetic analysis of chiral bioactive molecules. It will be divided in two parts: at the beginning the basics of stereochemistry and asymmetric metal- and organocatalysis will be introduced, followed then by the study of several total synthesis of chiral bioactive molecules and known drugs, based upon a stereoselective strategy. At the end of the course the students will be prepared to discuss various synthetic routes and perform retrosynthetic analysis of simple chiral molecules.
Full programme
1. CHIRALITY AND CHIRAL DRUGS (1.5 CFU)
1.1 Basic concepts of stereochemistry
1.2 Methods for the determination of stereisomeric composition
1.3 Methods for determining the absolute configuration of a chiral molecule
2. ASYMMETRIC SYNTHESIS OF CHIRAL, ENANTIOPURE MOLECULES (1.5 CFU)
2.1 Resolution
2.2 Chiral auxiliaries
2.3 Asymmetric, metal catalysis and organocatalysis
3. CHIRAL DRUGS THROUGH ASYMMETRIC SYNTHESIS (1 CFU)
3.1 Selected examples and "case studies" of total stereoselective synthesis of bioactive chiral molecules and commercial drugs.
Bibliography
All the reference material, will be provided by the teachers at the beginning of the course.
Suggested textbook:
J. CLAYDEN, N. GREEVES, S. WARREN, "Organic Chemistry", Second edition, Oxford 2012.
Teaching methods
The course will be carried out through frontal oral lessons (total 32 hours corresponding to 4 CFU) favoring active learning modalities using a dialogical relationship with the students. In the second part of each lesson, suitable exercises will be proposed dealing with the design, synthesis, and transformation of simple organic molecules which could be connected with the pharmaceutical and biological domains. These exercises are open for free discussion between teacher and students and they are considered an essential part of the course. Also several “case studies” will be analyzed following those criteria and methods described in the teaching and bibliographical material provided. All teaching slides will be uploaded weekly on Elly web-platform. All students willing to download the slides need to enlist first on the on-line course. These slides are considered to all intents and purposes important teaching material, as the books are. All students should always check on a regular basis the available material on the Elly-platform.
Assessment methods and criteria
The assessment of achievement of the training objectives involves a written report on a total and asymmetric synthesis of a chiral drug. This report, delivered at least 7 days before the scheduled call, is to be discussed in a dedicated oral test. More information about the oral test will be provided in class and communicated via the Elly platform.
Other information
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2030 agenda goals for sustainable development
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