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.

 

Course summary:

Date Details Due