KE814: Advanced organic synthesis (5 ECTS)

STADS: 10005401

Level
Master's level course

Teaching period
The course is offered in the spring semester.
The course is offered in the second half of the spring semester.

Teacher responsible

Email: trond@sdu.dk

Timetable

Group	Type	Day	Time	Classroom	Weeks	Comment
Common	I	Monday	10-12	U142	14
Common	I	Monday	10-12	U155	17
Common	I	Monday	10-12	U146	18
Common	I	Monday	10-12	U154	19
Common	I	Monday	13-15	U24A	25	Spørgetime
Common	I	Tuesday	12-14	U142	13-14,18-20
Common	I	Tuesday	10-12	U142	21
Common	I	Wednesday	10-12	U142	21
Common	I	Thursday	10-12	U142	17
Common	I	Thursday	10-12	U153	20
Common	I	Friday	10-12	U29A	13
H1	TE	Monday	14-16	U156	19
H1	TE	Monday	15-17	U56	22
H1	TE	Tuesday	14-16	U142	14,18,20-21
H1	TE	Friday	12-14	U28A	13

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Comment:
Samlæses med KE518

Prerequisites:
KE505 Organic chemistry or similar course is expected.

Academic preconditions:

Students taking the course are expected to:

Have good knowledge of systematic organic chemistry corresponding to KE505 Organic chemistry.

Course introduction

The aim of the course is to give the student a broad overview over reactions in organic chemistry and enable the student to design synthetic routes to given target molecules, which is important in regard to projects and/or careers within for example medicinal chemistry, material sciences and chemical production.

The participants will acquire broad knowledge to modern organic chemical reactions and their mechanisms and be able to design synthetic routes to complex target molecules such as drugs and natural products.

The course builds on the knowledge acquired in the 2nd year course KE505 Organic chemistry. It is also recommended that the material in KE526/KE823 Applied heterocyclic chemistry is known. The course gives an academic basis for bachelor and master projects that involves synthesis, for example within medicinal chemistry or material science.

In relation to the competence profile of the degree it is the explicit focus of the course to:

• Give the competence to plan synthesis projects.

• Give skills to design and plan synthetic routes to given target compounds.

• Give knowledge and understanding of organic chemical reactions and their theoretical basis and mechanisms.

Expected learning outcome

The learning objective of the course is that the student demonstrates the ability to:

Perform a retrosynthetic analysis of the structure of a given target molecule, e.g. a natural product or a pharmaceutical compound.
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 reaction conditions 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

Give mechanisms for the mentioned reactions
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

The following main topics are contained in the course:

Retrosynthesis and retrosynthetic analysis
Organic chemical reactions
The theoretical basis and mechanisms for the reactions

Literature

Clayden, Greeves and Warren: Organic Chemistry, 2nd edition, Oxford University Press, 2012.
Videnskabelige artikler og noter..

Website
This course uses e-learn (blackboard).

Prerequisites for participating in the exam
None

Assessment and marking:

4 hour written exam, danish 7-point grading scale, external examiner. A closer description of the exam rules will be posted under 'Course Information' on Blackboard. (5 ECTS). (10005402).

Expected working hours
The teaching method is based on three phase model.
Intro phase: 30 hours
Skills training phase: 14 hours, hereof:
- Tutorials: 14 hours

Educational activities

Study of the textbook and lecture slides
Solve problems that will be presented in the examination classes

Educational form
The teaching takes place as lectures where both slides and blackboard are used and with questions and problems distributed throughout the lectures. The students will work with problems at home that will be presented in the excercise classes. Towards the end of the course there will be focus on reterosynthesis and design of synthetic routes where the methods and reactions discussed previously will be used.

Language
This course is taught in Danish or English, depending on the lecturer. However, if international students participate, the teaching language will always be English.

Remarks

The course is co-read with: KE518
The course cannot be chosen by students who: Have passed KE518.
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.