KE814: Advanced organic synthesis (5 ECTS)

STADS: 10005401

Level
Master's level course

Teaching period
The course is offered in the spring semester.

Teacher responsible
Email: ulven@sdu.dk

Timetable
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Comment:
Samlæses med KE518.

Prerequisites:
None

Academic preconditions:
The bachelor degree in chemistry or with optional subject in chemistry or a bachelor degree in nanobioscience, pharmaceutical sciences, pharmacy or chemical engineering.

Course introduction
The participants will acquire knowledge to modern organic chemical reactions and ability to design synthetic routes to target molecules like natural products and medicinal drugs.

Expected learning outcome
By the end of the course it is expected that the participants will be able to:

• Perform a retrosynthetic analyze the structure of a given target molecule, e.g. a natural product or a pharmaceutical
• Design a synthetic route to the target molecule on basis of the retrosynthetic analysis
• Explain retrosynthetic terms (e.g. disconnection, functional group interconversion, synthon) and strategies (e.g. convergent vs. linear synthesis)
• Explain the purpose of protecting groups, give examples of protecting groups for functional groups like alcohols, amines, carboxylic acids, aldehydes and ketones, give conditions for their introductions and removal, and use them in design of synthetic routes.
• Demonstrate through understanding of the covered reactions as well as the basic reactions covered in the required basic organic chemistry course, including:
• Suggest reasonable reactions for given transformations
• Predict the outcome of a given reaction
• Propose a reasonable reaction mechanism
• The covered reaction types include
• Oxidations
• Reductions
• Substitution-, addition- and elimination reactions
• Alkylation of enolates and enamines (e.g. the aldol reaction)
• Pericyclic reactions (cycloadditions, sigmatropic and elektrocyclic reactions)
• Palladium catalyzed coupling reactions
• Olefin metathesis
• Explain chemoselectivity, regioselectivity and stereoselectivity (including diastereo- and enantioselectivity), and relate this to the covered reactions.
• Apply and discuss advanced new literature within synthetic organic chemistry.

Subject overview
By using published synthetic routes to natural products and medicinal drugs as starting point, the course will be directed at applied strategies in targeted organic synthesis. Retrosynthetic analysis, protecting groups and common modern organic chemical reactions like metal catalyzed coupling reactions, asymmetric synthesis, olefin metathesis, selective oxidation and reduction reactions, heterocyclic synthesis, cycloadditions and pericyclic reactions will be covered.

Literature

• Clayden, Warren, Greeves and Wothers: Organic Chemistry, Oxford University Press, 2000. Videnskabelige artikler og noter. .

Website
This course uses e-learn (blackboard).

Prerequisites for participating in the exam
None

Assessment and marking:
Oral exam, Danish 7-point grading scale, external examiner.

Reexamination in the same exam period or immediately thereafter. The mode of exam at the reexamination may differ from the mode of exam at the ordinary exam.

Expected working hours
The teaching method is based on three phase model.
Intro phase: 28 hours
Skills training phase: 14 hours, hereof:
 - Tutorials: 14 hours

Educational activities

Language
This course is taught in English, if international students participate. Otherwise the course is taught in Danish.

Remarks
This course is held together with the corresponding bachelor course KE518 Advanced organic synthesis.
The two courses are identical except for the prerequisites and the aim description.
If you plan to attend both Applied heterocyclic chemistry (KE526/KE823) and Advanced organic synthesis (KE518/KE814) in your complete study program, we recommend that you first attend KE526/KE823 or that you attend the two courses simultaneously.

Course enrollment
See deadline of enrolment.

Tuition fees for single courses
See fees for single courses.