UNIVERSITY OF WARWICK
Proposal Form for New or Revised Modules (MA1- version 4)
Approval information
Approval Type
Date of
Introduction/Change
New module
Discontinue module
Revised module
October 2011
If new, does this module
replace another? If so,
enter module code and
title:
If revised/discontinued,
Change of syllabus due to introduction of closely related material
please outline the rationale into third year modules, and recent developments in the subject.
for the changes:
Confirmation that affected
departments have been
consulted:
yes (n/a) no other departments affected.
Module Summary
1. Module Code (if known)
CH402
2. Module Title
Synthetic Chemistry I (Organic)
3. Lead department:
Chemistry
4. Name of module leader
Prof Martin Wills
5. Level
UG:
PG:
Level 4 (Certificate)
Level 6 (Honours)
Level 7 (Masters)
Level 5 (Intermediate)
Level 8 (Doctoral)
See Guidance Notes for relationship to years of study
6. Credit value(s) (CATS)
15 CATS
7. Principal Module Aims
This module is designed to develop student skills so that they will become
aware of current problems and directions in the forefront of Organic
Chemistry and consequently be able to critically evaluate current research
in this area. The module is also designed so that students will be able to
be original in application of their knowledge to the solutions to novel,
research led problems
This will be achieved by a range of teaching methods ranging from
student centred learning-including directed reading, workshops, and set
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Module Summary
exercises. Students will be expected to undertake a significant amount of
student centred learning around the subject which will be directed
appropriately during the 13 academic contact hours with the whole class.
An additional contact hour a week will be set aside (as bookable) so that
students who have concerns with directed reading and student centred
learning can discuss their problems with an academic on a one to one or
group basis.
The material will focus on the design and execution of the synthesis of
complex organic compounds, including natural products and
pharmaceutically important molecules. There will be a focus on the
strategy involved in the design of the syntheses, the use of
‘disconnections’ (working backwards from the target to identify starting
materials) and the use of protecting groups for sensitive functional
groups where appropriate. The issues of stereocontrol – both relative
and absolute – will be considered throughout the module.
Students will be expected to demonstrate their abilities by critical
evaluation of recent published material in one of the three areas of
study. This will be achieved by the submission of a written report.
Students will also undertake a written examination which will test both
their critical thinking around the subject as well as their ability to apply
their knowledge to original problems.
Students who take this module will obtain a sound overview of current
national and international research areas in synthetic organic chemistry
and will gain excellent training for careers in either academia or industry.
8. Contact Hours
(summary)
Lectures 10 hrs (1 per week)
Workshops 3 hrs (distributed over academic year)
Bookable Contact 10hrs (1 per week)
9. Assessment methods
(summary)
20% Written Work 2500 words
80% Examination
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Module Context
10. Please list all departments involved in the teaching of this module. If taught by more than
one department, please indicate percentage split.
Chemistry
11. Availability of module – the list below may need to be updated.
Degree Code
Title
Study Year
C/OC/
A/B/C
Credits
F105
Chemistry MChem
4
A
15 CATS
F106
Chemistry MChem with Professional
Experience
4
A
15 CATS
F107
Chemistry MChem with Intercalated
Year
5
A
15 CATS
F108
Chemistry MChem with Industrial
Training
4
A
15 CATS
F125
Chemistry with Medicinal Chemistry
MChem
4
A
15 CATS
F126
Chemistry with Medicinal Chemistry
MChem with Professional Experience
4
A
15 CATS
F127
Chemistry with Medicinal Chemistry
MChem with Intercalated Year
5
A
15 CATS
F128
Chemistry with Medicinal Chemistry
MChem with Industrial Training
4
A
15 CATS
FC11
Chemical Biology MChem
4
A
15 CATS
F1C1
Chemical Biology MChem with
Intercalated Year
5
A
15 CATS
AO VA
15 CATS
Visiting Students
12. Minimum number of registered students required for module to run
10
13. Pre- and Post-Requisite Modules
Pre-requisities
Normally, it would be expected that students had completed modules CH3E4 (Stereoselective
synthesis) and CH3E5 (reactive intermediates) or equivalent modules.
Module Content and Teaching
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Module Content and Teaching
14. Teaching and Learning Activities
Lectures
Seminars (workshops)
10hrs (1 per week)
3 x 1 hr workshops distributed throughout the module.
10hrs (1 per week bookable time)
Tutorials
Laboratory sessions
Total contact hours
23hrs
Module duration (weeks)
Other activity
10 weeks
Self Study/Revision 127hrs
(please describe): e.g.
distance-learning, intensive
weekend teaching etc.
15. Assessment Method (Standard)
Type of assessment
Examinations
Assessed
essays/coursework
Other formal assessment
Length
1.5 Hours
2500 Words
% weighting
80%
20%
Visiting Students AO VA
100%
16. Methods for providing feedback on assessment.
Marks for Examination to be provided via Personal Tutor. Feedback comments and grade on
assessed work provided on copy of marksheet.
17. Outline Syllabus
This module will be concerned with the design and execution of synthetic approaches to complex target
organic molecules, with reference to absolute and relative stereocontrol, disconnections and use of
protecting groups when appropriate. The selection of examples has been made with a view to including
many diverse examples of target structures, several of which are pharmaceutically significant, and a broad
range of synthetic chemistry reactions (which will have been taught in previous years).
Syllabus
A compulsory set of 10 lecture classes will be used to disseminate the material in the following areas.
1) Introduction to strategy, disconnections, retrosynthesis, protecting groups and extreme targets which
may include palytoxin, Vitamin B12, Brevitoxin, azadirachtin, vancomycin.
2) Early classics of total synthesis in organic chemistry, which may include colchicine, morphine,
strychnine, thienamycin and penicillin.
3) Lessons learnt from the synthesis of small important organic molecules which may include hirsutene,
periplanone B, epothilones and prostaglandins.
4) Molecules with a high degree of functionality, which may include avermectin, erythromycin,
Amphotericin B Strychnine.
5) Construction of highly complex structures which may include ginkolide B, calicheamycin, taxol.
6) The use of cycloadditions in complex molecule synthesis, which may include FR182877, estrone,
platensimycin, progesterone, daphniphylline alkaloids.
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Module Content and Teaching
7) Enantioselective strategies which may include biotin a-arylpropionic acids, menthol, zaragozic
acid, statins.
8) Peptide synthesis with emphasis on peptide bond formation, coupling reagents, orthogonal protecting
groups and solid phase synthesis. Relevant examples will include some natural peptides (e.g. oxytocin,
vasopressin and angiotensin; vancomycin and cyclosporins) and peptide-based drugs (e.g. angiotensin and
protease inhibitors, synthetic peptide hormones, enfuvirtide and eptifibatide).
9) Carbohydrate synthesis, with emphasis on glycosidic bond formation (including stereoelectronic effects
that influence the selectivity at the anomeric position) and the use of protecting groups.
10) Strategies for the synthesis of oligosaccharides. Relevant examples will include acarbose, heparins
and carbohydrate-based vaccines.
These classes will involve introductory ‘lecture’/seminars, and problem classes (workshops).
An additional contact hour a week will be set aside (as bookable) so that students who have concerns with
directed reading and student centred learning can discuss their problems with an academic on a one to
one or group basis.
18. Illustrative Bibliography
Because this is a research module the recommended texts are likely to be recently published research
articles and thus may change over the years.
Additional texts that are recommended
Books
Classics in Total Synthesis; K. C. Nicolaou and E. J. Sorensen, Wiley-VCH 1996. Classics in Total Synthesis II,
K. C. Nicolaou and E. J. Sorensen, VCH 2003.
Molecules that changed the world, K. C. Nicolaou and T. Montagnon, Wiley-VCH, 2008.
The Logic of Chemical Synthesis, E. J. Corey and X.-M. Cheng, Wiley-VCH, 1995.
S. Warren and P. Wyatt, Organic Synthesis: The Disconnection Approach, Wiley, 2nd Edn 2008 and the
associated workbook, 2nd Edition 2009.
Catalysis in Asymmetric Synthesis’ by V. Caprio and J. M. J. Williams, Wiley, 2010 (2nd Edition).
Amino acid and peptide synthesis, J. Jones, Oxford University Press, 2002 (2nd Edn.)
‘General Aspects of the Glycosidic Bond Formation’, A. V. Demchenko, from ‘Handbook of Chemical
Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance’, Wiley, 2008.
In addition, other annual reviews of progress frequently appear in review journals. For more detailed
reviews of particular areas, you can search the web of knowledge or Scifinder Scholar for comprehensive
literature surveys.
19. Learning outcomes
Successful completion of the module leads to the learning outcomes. The learning outcomes identify the
knowledge, skills and attributes developed by the module.
Learning Outcomes should be presented in the format ”By the end of the module students should be able
to...” using the table at the end of the module approval form:
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Resources
20. List any additional requirements and indicate the outcome of any discussions about these.
Approval
21. Module leader’s
signature
Prof Martin Wills
22. Date of approval
19th April 2011
23. Name of Approving
Committee (include minute
reference if applicable)
LTC
24. Chair of Committee’s
signature
Dr Andrew Clark
25. Head of Department(s)
Signature
Prof Mike Shipman
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Examination Information
A1. Name of examiner (if
different from module
leader)
Professor Martin Wills.
A2. Indicate all available methods of assessment in the table below
% Examined
% Assessed by other methods
Length of examination paper
80%
20%
1.5hrs
A3. Will this module be examined together with any other module (sectioned paper)? If so,
please give details below.
CH402X - CH402 and CH408
A4. How many papers will
the module be examined
by?
A5. When would you wish
the exam take place (e.g.
Jan, April, Summer)?
1 paper
2 papers
April
A6. Is reading time
required?
Yes
No
A7. Please specify any special exam timetable arrangements.
A8. Stationery requirements
No. of Answer books?
Graph paper?
Calculator?
Any other special
stationery requirements
(e.g. Data books, tables
etc)?
A9. Type of examination paper
Seen?
Yes
No
Open Book?
Yes
No
Restricted?
Yes
No
If restricted, please provide
a list of permitted texts:
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LEARNING OUTCOMES
(By the end of the module the student should be able
to....)
Understand and be aware of current research and problems
in the areas of total synthesis, including asymmetric
synthesis and stereocontrol in synthesis, as well as
disconnection and retrosynthetic strategies.
Use their knowledge to critically evaluate recent research
work in any of the three areas of study
To be able to disseminate that knowledge by the
preparation of a CONCISE written report. ( A concise report
will test the students ability for communicating/abstracting
only the MOST relevant material)
Show originality in application of their knowledge to solving
problems in the three areas of study
Which teaching and learning methods enable
students to achieve this learning outcome?
(reference activities in section 15)
Which summative assessment method(s) will
measure the achievement of this learning
outcome?
(reference activities in section 16)
Student directed learning, seminars, directed
reading, problems classes, set exercises, academic
office hours
Examination, Written Report
Student directed learning, seminars, directed
reading, problems classes, set exercises, academic
office hours
Examination, Written Report
Written Report
Student directed learning, seminars, directed
reading, problems classes, set exercises, academic
office hours
Examination.
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