Design and Synthesis Methods

Adquiring ability in using the most important types of organic reactions in retrosynthetic analysis.

Adquiring knowledge on the logic processes that allow the retrosynthetic analysis.

Learning the main concepts involved in retrosynthetic analysis.

Applying and being able to design strategies for the synthesis of relatively complex molecules.

Adquiring the ability to propose retrosynthetic schemes for the synthesis of natural products or molecules of interest in biology or material science.

1. Historic evolution of the organic synthesis.
Lineal synthesis and convergentsynthesis.
2. Basic concepts of Retrosynthetic analysis: synthon, donor and acceptor. Synthons, umpolung, consonants and disonants systems, tree of synthesis.
3.Retrosynthetic operators. Retron. Desconnection of monofunctionalizedcompounds: alcohols, alquenes, carbonyl compounds, carboxylic acids, C-C bonds. Retrosynthesis of simple molecules.
4. Retrosynthesis of difunctionalized and polifunctionalizedcompounds.
Retrosynthetic principles. Regiochemical and stereochemical issues. Strategic bond.
5 . Retrosynthesis of relatively complex molecules. Strategies based onfunctional groups. Strategies based on substructures. Strategies based on the molecular topology. Strategies based on the stereochemistry. Retrosynthesis of natural products.

Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley, Chichester, 1995.
E.J. Corey and Laszlo Kurti, Enantioselective Chemical Synthesis: Methods, Logic, and Practice, Direct Book Publishing LLC, 2010.
Fuhrhop, J.; Penzlin, G. Organic Synthesis: Concepts, Methods, Starting Materials, 2ndEd.; VCH, Weinheim, 1994.
Ho, T.-L. Tactics of Organic Synthesis, Wiley & Sons. New York, 1994.
Warren, S. Organic Synthesis: The Disconnection Approach2ndEd.; Wiley, Chichester, 2008.
Warren, S.; Wyatt, P. Workbook forOrganic Synthesis: The Disconnection Approach; Wiley& Sons. New York 2009.
Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis: Targets, Strategies, Methods;VCH, Weinheim, 1996.
Nicolaou, K. C.;Snyder, S. A. Classics in Total Synthesis II: Targets, Strategies, Methods. Ed. Wiley, 2003.
Nicolaou, K. C.; Chen, J. Classics in Total Synthesis III: Further Targets, Strategies, Methods; Wiley-VCH, Weinheim, 2011.

Specific competences.

CE1 - To know the most relevant organic synthesis methods, including the fundamentals of stereoselective processes in organic chemistry, and to be able to design routes of synthesis of complex organic molecules


Transversal competences.

CT4 - Apply the concepts, principles, theories or models related to Organic Chemistry to new or little known environments, within multidisciplinary contexts.

Theoretical lectures:
In-class lessons, whereby the theoretical concepts and contents of the course will be disclosed. The contents of these lessons will be applied to solve exercises and problems during seminars.
In these theoretical lectures the students will also solve brief practical exercises as direct application of the theoretical concepts.

The weight of components of the final grade will be as follows:
Exam calification 50%
Additional calification 50%:
Problem resolution during seminars 20.0
Resolution of exercices out-class 20.0
Active participation and discussion 10.0

In-class work
Theoretical lessons: 24 h
Exam: 3 h
Total : 27 h
Personal out-class work
Weekly study (for the whole course), out-class exercices and exam preparation : 48 h
Total: 75 h (3 ECTS)

Class attendance is essential since a large number of practical examples are used to help the student become familiar with the retrosynthetic analysis. It is also necessary for the student to work out the exercises proposed for the home.
Of course, it is important to handle with ease the main types of organic reactions.