SubjectsSubjects(version: 855)
Course, academic year 2019/2020
  
Retrosynthesis - D110004
Title: Retrosyntéza
Guaranteed by: Department of Organic Chemistry (110)
Actual: from 2017
Semester: summer
Points: summer s.:0
E-Credits: summer s.:0
Examination process: summer s.:
Hours per week, examination: summer s.:0/0 other [hours/week]
Capacity: unknown / unknown (unknown)
Min. number of students: unlimited
Language: Czech
Teaching methods: full-time
Level:  
For type:  
Additional information: http://uoch.vscht.cz/files/uzel/0006592/synton.pdf
Note: course is intended for doctoral students only
Guarantor: Cibulka Radek prof. Ing. Ph.D.
Is interchangeable with: AP110004, P110004
Examination dates   Schedule   
Annotation -
Last update: Cibulka Radek prof. Ing. Ph.D. (23.06.2018)
The aim of this course is introduction of the disconnection approach to organic synthesis. This approach is analytical: we start with the molecule we want to make (the target molecule) and break it down by a series of disconnections into possible starting materials. During the course, the retrosynthetic method is shown on simple as well as on more complicated structures which are known from practical life: pharmaceuticals, pesticides, dyes, perfumes etc.
Aim of the course -
Last update: Cibulka Radek prof. Ing. Ph.D. (23.06.2018)

Students will be able to:

Use nomenclature of retrosynthetic analysis

Plan synthesis of multifunctional compounds

Apply algoritms of retrosynthetic analysis to design synthesis of complex compounds

Evaluate the best synthetic pathway

Literature -
Last update: Cibulka Radek prof. Ing. Ph.D. (23.06.2018)

R: Warren S., Wyatt P.: Organic synthesis - The disconnection approach, 2nd Edition, John Wiley, 2008, 9780470712368

R: Warren S., Wyatt P.: Workbook for Organic Synthesis: The Disconnection Approach, 2nd Edition, John Wiley, 2009, 9780470712276

A: Wyatt P., Warren S.: Organic Synthesis - Strategy and Control, John Wiley, 2007, 9780470489405

Learning resources -
Last update: Cibulka Radek prof. Ing. Ph.D. (03.04.2014)

http://uoch.vscht.cz/cz/download/synton.pdf

Syllabus -
Last update: Cibulka Radek prof. Ing. Ph.D. (23.06.2018)

1. The disconnection approach. Basic principles. Transformations.

2. Synthons and their preparation. Umpolung, logical and nonlogical synthons.

3. One group C-X disconnections.

4. Two group C-X disconnections.

5. One group C-C disconnections in oxidation state of alcohols.

6. One group C-C disconnections in oxidation state of ketones.

7. Alkene and alkyne synthesis. Synthesis of biaryls.

8. Two group disconnections - introduction. C-C disconnection in 1,3- and 1,5-difunctionalised compounds.

9. Synthesis of 1,2-, 1,4- and 1,6-difunctionalised compounds.

10. Strategy of ring synthesis. Baldwin's rules.

11. Synthesis of cyclobutane and cyclopentane derivatives.

12. Synthesis of cyclopentane and cyclohexane derivatives and of the compounds with large ring.

13. Heterocyclic compounds - classification. Synthesis of heterocyclic and heteroaromatic compounds.

14. Multistep synthesis of natural compounds.

Course completion requirements -
Last update: Cibulka Radek prof. Ing. Ph.D. (23.06.2018)

It is compulsory to prepare project on the synthesis of natural compound, to pass written examination test with the result at least 60%, and finally to pass successfuly the oral examination.

Coursework assessment
Form Significance
Examination test 50
Oral examination 50

 
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