Course syllabus

Course-PM

KBT160 Advanced organic synthesis lp4 VT20 (7.5 hp)

Course is offered by the department of Chemistry and Chemical Engineering

Contact details

Examiner and teacher on the course

Jerker Mårtensson

Email: jerke@chalmers.se

Phone: 3071

Office: 9024

Teachers

Nina Kann

Email: kann@chalmers.se

Phone: 3070

Office: 9075

Carl Johan Wallentin

Email: carl.johan.wallentin@gu.se

Phone: 031-786 9045

Office:

Course purpose

Complex molecules, such as drugs, polymers, detergents, and natural products, are an innate part of everyone’s daily life. Whether in an academic or in an industrial environment, the assembly of such complex molecules from simple and readily available compounds plays an integral and indispensable role in its development. Advanced Organic Synthesis is a course which explores the challenges posed by the assembly processes, i.e. the syntheses, by which complex molecules are constructed. It aims to equip the student with the necessary tools for efficient planning of successful synthetic routs to new compounds with improved or new desirable properties. It aims to provide the student with a thorough knowledge and understanding of:

• Retrosynthetic analysis.
• Analysis of selectivity and stereochemical problems.
• Functional group interconversion and protective group methodology.
• Modern methods for carbon-carbon, and carbon-heteroatom bond formations.
• Safety and health aspects of reagents and chemical transformations.

Schedule

The course starts with an introductory lecture on Thursday, March 27, between 9 and 12 a.m. in lecture room 8052.

Preliminary schedule shown below.

Date	Time	Lecture/Activity
Week 13
Thursday 26 Mars	9-12	Introduction, Tips and info
Friday 27 Mars	15-16	More than just using bigger flasks – Scale up of the 2nd generation DPP1 inhibitor AZD7986
Week 14
Mon 30	13-16	Retrosynthetic analysis
Tuesday 31 Mars	9-12	Protecting groups
Thursday 2 April	9-12	Transition metals in catalysis
Friday 3 April	15-17	Carbenes, amines and acids in catalysis
Week 15
Monday 6 April		Re exam week
		Re exam week
Thursday 9 April		Maundy Thursday
Friday 10 April		Good Friday
Week 16
Monday 13 April		Easter Monday
Thursday 16 April	9-12	Conformational Analysis: applications in asymmetric synthesis
Friday 17 April	15-17	Radicals in synthesis
Week 17
Monday 20 April	13-16	Biyouyanagin A
Thursday 24 April	9-12	Discodermolide
Week 18
Monday 27 April	13-16	Tetrodotoxin
Thursday 30 April	9-12	Azaspiracid-1
Week 19
Monday 4 May	13-16	Pentacycloanammoxic Acid Methyl Ester
Thursday 7 May	9-12	Vannusal B
Week 20
Monday 11 May	13-16	Rubicordifolin and Rubiconcolin B
Thursday 14 May	9-12	Cyanthiwigins U and F
Week 21
Monday 18 May	13-16	Stephacidin B
Thursday 21 May	9-12	“Kristi himmelfädsdagen”
Week 22
Monday 25 May	13-16	Tetracycline
Thursday 28 May	9-12	Bisanthraquinone
Friday 29 May
Week 23
Monday 1 June	13-16	Welwitindolinone A
Thursday 4 June	9-12
Friday 5 June	9-12	*Halophytine & course evaluation

Course literature

Classics in total synthesis III by Nicolaou and Chen, Wiley (ISBN: 978-3-527-32958-8, ISBN-13: 978-3527329571).

Supplementary Text(s)

Organic Chemistry, J. Clayden, N. Greevs, S. Warren, and P. Wothers, Oxford University Press; Organic Chemistry, T. W. G. Solomons and C. B. Fryhle, WILEY.              

Course design

The course is primarily a seminar (9 × 3 h) course, supported by lectures (16 × 45 min) that cover the more general concepts. One purpose of the seminars is to help to understand the concepts that have been introduced in lectures and to show how they are used in practice. Another is to expose the student to a plethora of modern synthetic methods applied in real contexts. The participants are expected to be thoroughly familiar with the topic discussed at the seminar and completely prepared to participate in the discussion and to present assigned topics.

Changes made since the last occasion

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Learning objectives and syllabus

Learning objectives:

• Apply a retrosynthetic approach to the design of efficient multi step routes to complex organic molecules.
• Identify potential selectivity issues, and suggest appropriate synthetic methods and protective groups to circumvent them.
• Evaluate the proposed routes with respect to the availability of suitable starting materials.
• Evaluate the proposed routes with respect to environmental and health aspects.
• Suggest and evaluate a large number of modern synthetic methods for functional group inteconversions, and for the formation of new carbon-carbon or carbon-heteroatom bonds.
• Retrieve information from the original literature about the underlying mechanisms and experimental conditions for the reactions applied in synthesis of complex molecules.
• Identify key steps in the synthetic routes and effectively communicate the rationales for the applied experimental procedures based on the underlying reaction mechanisms.

Link to the syllabus on Studieportalen.

Study plan

Examination form

There is no final examination. The assessment is continuous and integrated and based on:

• written in-class tests at each group seminar,
• written and oral presentations,
• the degree of active participation in discussions at the seminars, and
• attendance.

To pass the course the student must attend at least 75% of the seminars. In addition, the student must have 50% or more correct answers on all the in-class tests combined. The grade of the whole course is given as a weighted average of the different components according to:

                      SUM = 100 x (0.45 x SD + 0.1 x ADD+ 0.05 x MQ + 0.40 x ST)

SD = group seminars given by the student, ADD = active participation in the group discussions following the seminars, MQ = mail in questions, ST = seminar tests.

The minimum passing score is 50% of the maximum total marks (SUM = 100). More than 67% corresponds to grade 4, and more 83% correspond to grade 5.