Organic chemistry

LECTURE. Organic synthesis - introduction: planning of synthesis, selectivity of the reactions and control of their stereochemistry. Basic principles of retrosynthetic analysis: definitions and terminology. Types of disconnections. Donor and acceptor synthons. Functional group interconversion (FGI). Formations of bonds: C-C and C-X. Protective groups: introduction and removal and strategy for choosing. Asymmetric synthesis. Synthesis with the use of chiral auxiliary, reagent and catalyst. Organic synthesis with the use of organophosphorus compounds: Wittig reaction (phosphorus ylides), Horner-Wodsworth-Emmons reaction and Mitsunobu reaction. Organic synthesis with the use of organosulfur compounds. Synthesis of complex molecules. Polar rearrangements. LABORATORY. Exercises involve multistep syntheses with emphasis on their planning, retrosynthetic analysis and selection of protective groups. Examples of Wittig and Mitsunobu reactions.

The aim of the subject is to provide knowledge of modern planning of organic syntheses with regard to retrosynthetic analysis, including planning of synthesis of chiral compounds. LEARNING OUTCOMES. On completion of the course students should know how to plan the synthesis of medium complex organic compounds with the use of retrosynthetic analysis and chiral compounds employing chiral auxiliaries, reagents and catalysts. Moreover, students should posses skills to perform multistep synthesis using protective groups.

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2) Carrey F. A. and Sundberg R. J., Advanced Organic Chemistry, Springer (2007).

3) Smith M. B., Organic Synthesis, McGraw-Hill, New York (2002).

4) Warren S., Organic Synthesis: The Disconnection Approach, John Wiley and Sons, New York (1982).