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Retrosynthesis and Total Synthesis of Organic Compounds - MC270P92

Title:	Retrosyntéza a totální syntéza organických látek
Czech title:	Retrosyntéza a totální syntéza organických látek
Guaranteed by:	Department of Organic Chemistry (31-270)
Faculty:	Faculty of Science
Actual:	from 2020
Semester:	winter
E-Credits:	2
Examination process:	winter s.:
Hours per week, examination:	winter s.:1/1, Ex [HT]
Capacity:	unlimited
Min. number of students:	unlimited
4EU+:	no
Virtual mobility / capacity:	no
State of the course:	taught
Language:	Czech, English
Note:	enabled for web enrollment

Guarantor:	PharmDr. Eliška Matoušová, Ph.D.
Teacher(s):	doc. Ing. Josef Hájíček, CSc. prof. RNDr. Martin Kotora, CSc. PharmDr. Eliška Matoušová, Ph.D. prof. RNDr. Jan Veselý, Ph.D.
Pre-requisite :	MC270P13A

Opinion survey results Examination dates WS schedule

Annotation -

Last update: PharmDr. Eliška Matoušová, Ph.D. (12.10.2020)

The lecture combined with seminar introduces basic principles of the planning of organic syntheses by using so-called retrosynthetic analysis. This process includes mental transformation of target molecules into simpler precursors (synthons), which operation is repeated until the synthons represent commercially available compounds.
The second part of the course will be devoted to the application of this approach in the synthesis of complex organic molecules and compounds with biological properties.

Literature - Czech

Last update: PharmDr. Eliška Matoušová, Ph.D. (06.10.2023)

Liška F.: Organická syntéza - syntonový přístup, VŠCHT Praha 1993, 807080176X

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

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

Wyatt P., Warren S.: Organic Synthesis: Strategy and Control, 1st Edition, John Wiley, 2007, 9780471929635

Requirements to the exam -

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.08.2021)

During the semester it is mandatory to complete and hand in a Seminar work of the required quality, which will deal with a retrosynthetic analysis of an assigned natural product (ca 50% of overall evaluation).

The exam will be in a form of written test with a following short oral discussion (ca 50% of overall evaluation), both on the topics covered by lectures and seminars (maximum three attempts).

At least 60% points must be acquired from both parts (seminar work and exam).

Syllabus -

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.08.2021)

1. Basics concepts and principles of retrosynthetic analysis. Definition of synthons, synthetic equivalents of synthons (Dr. Matoušová)

2. One-group and two-group carbon-heteroatom disconnections (Dr. Matoušová)

3. One-group carbon-carbon disconnections (Dr. Matoušová)

4. Two-group carbon-carbon disconnections (Dr. Matoušová)

5. Retrosynthesis of medium-sized rings (Dr. Matoušová)

6. Using of retrosynthetic principles in the total synthesis of biologically active compounds (Dr. Matoušová)

7. History of total synthesis of natural products (doc. Hájíček)

8. Retrosynthesis of small rings, total syntheses of monocyclic (including heterocyclic) natural products with 2 to 3 functional groups (doc. Veselý)

9. Retrosynthesis of large rings, total syntheses of macrocyclic natural products (doc. Hájíček)

10. Umpolung chemistry (doc. Veselý)

11. Synthesis of helicenes a cyclophanes (prof. Kotora)

12. Stereoselectivity (Dr. Matoušová)

Entry requirements -

Last update: PharmDr. Eliška Matoušová, Ph.D. (21.08.2023)

The course is intended for MSc students in the second year of their study and for PhD students. The entrance knowledge of organic chemistry at the level of Organic Synthesis I - III is expected. MSc students are required to have successfully completed the course Organic Synthesis I (MC270P13A) prior to enrolling in this course.