In the middle of the last century Woodward, Robinson and Eschenmoser described how synthesis of more complex molecules could be accomplished using a logical methodology which was named by Corey as retrosynthesis. Today most of synthetic problems are solved by such retrosynthetic analysis that breaks down the target molecule into simple, commercially available starting materials. In the framework of this class, different approaches to organic synthesis planning will be considered, including how to find a suitable starting substrate and applicable chemical reactions for the construction of target molecules as well as retrosynthetic transformations of the target molecule into synthetic precursors. The most common synthon types that are used to build up the carbon skeleton of more complex molecules will also be mentioned. Additionally, the class will focus on functional group transformations and reactions responsible for the construction of carbon-carbon bonds that are of special interest in organic synthesis. Topics that will be discussed include stereochemistry and conformations, control of stereochemistry during ring formation reactions, protecting groups, pericyclic, electrophile and radical reactions, oxidations and reductions, etc., as well as selected examples dealing with construction of bigger, more complex molecules.
1. Expanding basic knowledge of the organic compounds synthesis.
2. Defining and explaining general concepts of retrosynthetic analysis.
3. Classifying construction and transformation reactions necessary for preparation of more complex molecules.
4. Defining appropriate synthons for application in synthesis and describing their synthetic equivalents.
5. Applying the retrosynthetic approach in the construction of target molecules and planning of their synthesis.
Teaching and examinations: lectures, seminars and consultations
- OBVEZNA LITERATURA:
P. Wyatt, S. Warren, Organic Synthesis: Strategy and Control, Wiley, Chichester, England, 2007
W. A. Smit, A. F. Bochkov, R. Caple, Organic Synthesis: The Science behind the Art, RSC, Thomas Graham House, Cambridge, 1998.
E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989.
- DOPUNSKA LITERATURA:
T. A. Hase, Umpoled Synthons: A Survey of Sources and Uses in Synthesis, Wiley, New York, 1987.
B. M. Smith, Organic Synthesis: Theory, Reactions and Methods, McGraw-Hill, 1994.
D. Lednicer, Strategies for Organic Drug Synthesis and Design, Wiley, New York, 1998.
B. M. Smith, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition, Wiley, New York, 2013.