The competencies that the students need to acquire are detailed on Webcampus and will form the basis of the evaluation.
This laboratory course presents the students for the first time with the task of tackling a multistep synthesis. Furthermore, they will expand their practical capabilities in the laboratory and further advance in their application of modern spectroscopic methods to the structural characterisation of organic molecules. A particular challenge will be the setting up of air- and moisture-sensitive reactions under inert atmosphere and the handling or pyrophoric organolithium reagents.
The students will tackle the multistep synthesis of a resorcylic acid lactone natural product (lasiodiplodin).
Planning and setting up of a concise multi-step synthesis of lasiodiplodin.
1. Vilsmeier-Haack formylation of orcinol
2. Double phenol methylation of the orsellinic aldehyde
3. Lindgren-Pinnick oxidation : dimethylorsellinic acid
4. Benzylic alkylation of the orsellinic acid derivative
5. Mitsunobu ester formation of the orsellinic acid derivative
6. Macrocylisation by ring-closing alkene metathesis
7. Palladium-catalysed hydrogenation of the macrocyclic alkene
8. Demethylation of a phenolic ether: synthesis of lasiodiplodin.
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Students are assessed via the reports they write on the experiments carried out in the lab, in addition to a general assessment of their behaviour in the laboratory.
To validate the course, students must participate in all laboratory sessions.
Any absence must be justified (by an official document that needs to be presented to the secretary of the Faculty of Science in the required timeframe). In the absebce of justification, the respective laboratory session will receive a mark of 0/20.
If the absence was justified, the student may be asked to hand in a written report for each day of laboratory work they have missed. The subject of the report will be linked to the missed practical work and will be based on a scientific publication or data provided by the lecturer/assistant.
A syllabus is provided.
| Training | Study programme | Block | Credits | Mandatory |
|---|---|---|---|---|
| Bachelier en sciences chimiques | Standard | 0 | 4 | |
| Bachelier en sciences chimiques | Standard | 3 | 4 |