Panning syntheses of active compounds 0600-S1-CM-PW7b-PSZA

Lecture
Introduction: the essence of organic syntheses, historical background, key stages in the development of the field, branches of the field: combinatorial chemistry, total synthesis and the design of new synthetic procedures, goals, practice and assumptions of total synthesis, presentation of the basic concepts of retrosynthetic analysis on various reaction examples (target molecule, transformation, retron, disconnection, synthon, reagent, decision tree for retrosynthetic analysis).
Basic assumptions of retrosynthetic analysis: synthons, types of synthons, acceptor and donor synthons, masking the reactivity of functional groups, hidden polarization, target molecules with two functional groups – consonant and dissonant patterns, inversion of polarization, umpolung synthons and their synthetic equivalents.
Functional group transformations: carbon atom oxidation states, types of transformations occurring without the change in the oxidation state (type 1) and with the change in the oxidation state of the carbon atom (type 2), oxidation and reduction reactions, synthesis of cyclic compounds, Baldwin rules, Robinson anelation, Diels-Alder reaction.
Strategies of planning syntheses: linear and convergent synthesis, disconnections, symmetry of the molecule, functional group introduction, selection of the most efficient synthetical route.
Efficiency and selectivity of organic syntheses: chemoselectivity, chemoselective oxidation, chemoselective reduction, atom economy, protecting groups of alcohols and amines, stereoselectivity, regioselectivity, kinetic reaction control, thermodynamic reaction control, alkene synthesis – position of the double bond, cis-trans isomerism, alcohol dehydratation, reduction of alkines, Wittiga/Hornera-Wadswortha-Emmonsa reaction, synthesis of alcohols, hydration, oxymercuration/demercuration reaction, borohydration/oxidation, regioselectivity of aromatic electrophilic substitution, regioselectivity of ketone alkylation, regioselective nucleophilic addition to α,β-unsaturated carbonyl compounds, regioselective nucleophilic addition to epoxides, regioselective oxidation of ketones to esters - Baeyera-Villigera reaction.
Selected organic syntheses: a summary of the acquired knowledge about retrosynthetic analysis presented on selected examples of multi-step syntheses of active compounds; presentation of a practical application of the described synthetic methods.

Exercises
These classes are devoted to solving problems in the field of organic synthesis using the principles of retrosynthetic analysis presented in the lecture. The basis of the course will be the search for appropriate synthetic pathways in order to design a multi-step syntheses of the target bioactive molecules.