COURSE CONTENT:
Making alive the knowledge of organic and physical organic chemistry from the former courses enables planning of the synthesis of organic molecules of various complexity is discussed. This planning is based on the retrosynthetic analysis, or disconnection approach as introduced by Warren (1,2). Mechanistic aspects of most important synthetic transformations are discussed in relation to the concept of stable synthons, in particular for the carbon-carbon bond forming reactions. In this context charge alternation principle, and definition of obvious and non-obvious (?non-logical?) synthetic equivalents or reagents are presented. The importance of the modern, catalytic synthetic methods as the source of functional groups and their interconversions is revealed (3). Characteristics of laboratory scale and industrial scale synthetic conditions and protocols are emphasized.
LEARNING OUTCOMES:
After completion of this course, the successful student will be able to:
- define and to explain the basic concepts of retrosynthetic analysis (target molecule, disconnection, synthon and synthetic equivalent)
- specify, to explain and to apply retrosynthetic tools (disconnection, functional group interconversion, functional group addition etc.) in retrosynthetic analysis of target molecules
- classify and to analyze retrosynthetically target molecules with respect to the position of functional groups (1,2-, 1,3-, 1,4-, 1,5- and 1,6-difunctionalised compounds)
- identify synthetic equivalents based on the structure of synthons
- plan and twrite the synthesis of organic molecules based on retrosynthetic analysis
- expand the knowledge of organic chemistry and apply them in solving problems.
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- 1. S. Warren, Designing Organic Synthesis, A Programmed Introduction to the Synthon Approach, 5. izdanje, J. Wiley & Sons, 1989.
2. S. Warren, P. Wyatt, Organic Synthesis, The Disconnection Approach, 2. izdanje, J. Wiley & Sons, 2008.
3. S. Warren, Workbook for Organic Synthesis, 4. izdanje, J. Wiley & Sons, 1989.
- F. A. Carey, R. J. Sundberg: Adanced Organic Chemistry, Part. B: Reactions and Synthesis, Kluwer Academic/Plenum Publishers, 2001, posebno poglavlja 8-10 i 13.
- J. March: Advanced Organic Chemistry, Reactions, Mechanisms and Structure, 4. izdanje, Wiley, New York, 1992, posebno poglavlja 5, 6, 8 i 9.
- F. Serratosa, J. Xicart: Organic Chemistry in Action, The Design of Organic Synthesis, Elsevier, 1996.
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