| Topic |
Sub-topic |
| 1. THE DESIGN OF ORGANIC SYNTHESIS. RETROSINTHETIC ANALYSIS |
1.1. Introduction to target-oriented synthesis.
1.2. Rethrosynthetic analysis. The synthon approach. Transforms and rethrons. Strategic disconnections. The synthesis tree.
i. Preliminary evaluation.
ii. Simplifying transforms.
iii. Powerful transforms.
iv. Interconversion, addition and removal of functional groups.
1.3. Computer-based synthetic strategies.
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| 2. CRITERIA OF SELECTION OF DISCONNECTIONS |
2.1. One- and two-group C-X disconnections (1,n).
i. Synthons snd synthetic equivalents.
ii. Alternate polarities.
iii. Inversion of polarity.
iv. Functional groups interconversions.
v. Addition and removal of functional groups.
2.2. One- and two-group C-C disconnections (1,n).
i. One-group C-C disconnections.
ii. (1,n) C-C disconnections of difuncionalized compounds.
2.3. Tactics of skeletal transformations. Rearrangements and fragmentations.
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| 3. FUNCTIONAL GROUPS INTERCONVERSIONS |
3.1. Interconversion of functional groups by substitution, addition and elimination.
3.2. Oxidation reactions.
i. Transition metals (*Cr and *Mn).
ii. Methods based in the generation of "activated DMSO".
iii. Hypervalent iodine reagents.
iv. Olefin epoxidation and dihydroxylation.
3.3. Reduction reactions.
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| 4. CHEMOSELECTIVITY. PROTECTIVE GROUPS IN ORGANIC SYNTHESIS |
4.1. Strategies for the selection of protective groups: orthogonal or of modulated sensitivity .
4.2. Description of protective groups.
i. Sensitive to acids or bases.
ii. Sensitive to fluoride.
iii. Sensitive to reduction and oxidation reagents .
iv. Other protective groups.
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| 5. STEREOCHEMICAL STRATEGIES . STEREOSELECTIVITY |
5.1. Description of Stereochemistry.
i. Symmetry and chirality. Stereogenic units.
ii. Topicity.
iii. Relative configuration. Descriptors.
5.2. *Stereochemistry in chemical reactions.
i. Product selectivity.
ii. Simple- and induced-distereoselectivity.
5.3. Disconnections based in chiral fragments.
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| 6. DISCONNECTIONS OF UNSATURATED COMPOUNDS |
6.1. Stereoselective olefin synthesis .
i. Carbanions stabilised by phosphorous: Wittig and HWE reactions.
ii. Carbanions stabilised by silicon: Peterson reaction.
iii. Carbanions stabilised by sulphur: Julia reaction.
iv. Claisen rearrangement.
v. Olefin metathesis.
6.2. Palladium-catalyzed reactions.
i. Heck reaction.
ii. Stille, Negishi and Suzuki cross-coupling.
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| 7. FORMATION AND REACTIVITY OF CYCLIC COMPOUNDS. TOPOLOGICAL STRATEGIES |
7.1. Formation of saturated carbocyclic and heterocyclic compounds.
i. Cyclization reactions. The Thorpe-Ingold effect.
ii. Baldwin Rules.
iii. Formation of carbocyclic compounds.
7.2. Formation of heterocyclic compounds.
i. (3+2) Cycloadditions.
ii. Condensation of dicarbonyl compounds.
7.3. Properties and reactivity of aromatic heterocyclic compounds.
7.4. Topological strategies in Retrosynthetic Analysis.
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| LAB EXPERIMENT 1. Preparation of a-D-glucopyranoside pentaacetate |
One session |
LAB EXPERIMENT 2. Preparation of b-D-glucopyranoside pentaacetate
|
Two sessions |
LAB EXPERIMENT 3. Reactivity of dimethylsulfoxonium methylide with conjugated and nonconjugated carbonyl compounds: synthesis of epoxides and cyclopropanes.
|
One session |
| LAB EXPERIMENT 4. Microwave-assisted Diels-Alder reaction |
One session |
| LAB EXPERIMENT 5. Preparation of an Ionic Liquid. Application in the synthesis of coumarines |
Two sessions |
| LAB EXPERIMENT 6. Suzuki reaction in water |
One session |
| LAB EXPERIMENT 8. Total synthesis of a natural product: caffeic acid phenethyl ester (CAPE) |
Four sessions |
