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Organic Synthesis and Drug Design

Module description

This module brings together all the organic chemistry studied in previous modules to show how we devise syntheses of complex organic molecules (with particular emphasis on drug molecules) for uses ranging from small scale, in the research laboratory, to large industrial scales. You will learn how to devise routes to new molecules, using an approach that simply "reverse engineers" the final structure. Selective methods for interchanging functional groups by reduction and oxidation will also be added to the range of chemical transformations you need to complete your synthetic schemes, and modern methods for minimising waste and environmental pollution problems in organic chemistry will be explained.

Module aims - intentions of the module

This module aims to show how, with the addition of some new reagents and reactions to those already studied in earlier modules, multi-step syntheses of complex biologically important molecules (e.g. pharmaceuticals) can be devised. By placing an emphasis on selectivity (chemo- and stereo-), you will discover how to select appropriate reagents for specific synthetic transformations and how to provide mechanistic explanations for these reactions. The module also aims to introduce the basic principles of retrosynthetic analysis and show how these are used to devise multi-step syntheses. It also aims to show how modern synthetic procedures such as combinatorial/parallel synthesis and "environmentally friendly" reagents and methodologies can be incorporated into organic synthesis.

Intended Learning Outcomes (ILOs)

ILO: Module-specific skills

On successfully completing the module you will be able to...

• 1. Evaluate and choose appropriate reducing or oxidising agents for selective functional group transformations
• 2. Design protecting group strategies to enable chemoselective transformations to be carried out
• 3. Perform retrosynthetic analysis on complex organic molecules
• 4. Devise multi-step syntheses of complex organic molecules
• 5. Discuss the mechanisms of important organic transformations
• 6. Explain how synthetic procedures can be modified to allow the simultaneous generation of a wide range of structurally related compounds and address environmental issues

ILO: Discipline-specific skills

On successfully completing the module you will be able to...

• 7. Evaluate in detail approaches to our understanding of organic chemistry with reference to primary literature, reviews and research articles
• 8. Analyse in detail essential facts and theory in a subdiscipline of the chemical and biosciences
• 9. Analyse and evaluate independently a range of research-informed literature and synthesise research-informed examples from the literature into written work
• 10. With limited guidance, deploy established techniques of analysis and enquiry within the chemical and biosciences

ILO: Personal and key skills

On successfully completing the module you will be able to...

• 11. Communicate effectively arguments, evidence and conclusions using written and oral means in a manner appropriate to the intended audience
• 12. Devise and sustain, with little guidance, a logical and reasoned argument with sound, convincing conclusions
• 13. Analyse and evaluate appropriate data with very limited guidance

Syllabus plan

The concept of oxidation level in the context of organic functional groups will be introduced and exemplified with hydrocarbons, oxygen and nitrogen-containing groups and organic halides, along with a reminder of the definitions of chemo-, regio- and stereoselectivity. Examples of commonly encountered reduction methods/reagents will be given, including catalytic hydrogenation, dissolving metal reduction, hydride-transfer reagents and Wolff-Kishner reduction.

Oxidation will be approached from the perspective of the functional group being oxidised. This section of the module will cover oxidation of alcohols, aldehydes, ketones and alkenes.

Issues of chemoselectivity will be addressed in an examination of the most important protecting groups for alcohols, aldehydes, ketones, carboxylic acids and amines.

The synthesis of polyfunctional organic molecules will be introduced using a retrosynthetic analysis. Standard "disconnections" will be covered, along with the appropriate "synthons".

The central concept of carbon-carbon single bond formation for the construction of complex molecules will be illustrated with the use of organometallic reagents, carbanions and enolates. The formation of carbon-carbon double bonds will also be covered by an introduction to Wittig, Horner-Wadsworth-Emmons and Julia reactions.

Learning activities and teaching methods (given in hours of study time)

Details of learning activities and teaching methods

Formative assessment

Summative assessment (% of credit)

Details of summative assessment

Details of re-assessment (where required by referral or deferral)

Re-assessment notes

Deferral – if you miss an assessment for certificated reasons that are approved by the Mitigation Committee, you will normally be either deferred in the assessment or an extension may be granted. If deferred, the format and timing of the re-assessment for each of the summative assessments is detailed in the table above ('Details of re-assessment'). The mark given for a deferred assessment will not be capped and will be treated as it would be if it were your first attempt at the assessment.

Referral - if you have failed the module (i.e. a final overall module mark of less than 40%) and the module cannot be condoned, you will be required to complete a re-assessment for each of the failed components on the module. The format and timing of the re-assessment for each of the summative assessments is detailed in the table above ('Details of re-assessment'). If you pass the module following re-assessment, your module mark will be capped at 40%.

Indicative learning resources - Basic reading

• J. Clayden, N. Greeves and S. Warren, Organic Chemistry (Second Edition), Oxford University Press, 2012, ISBN 0-19-927029-5 (essential core text)
• C. Willis and M. Wills, Organic Synthesis, (Oxford Chemistry Primer 31), Oxford University Press, 1995, ISBN 0-19-855791-4

Indicative learning resources - Web based and electronic resources

• ELE page: https://vle.exeter.ac.uk/course/view.php?id=9255

Key words search

Molecules, reduction, oxidation, synthetic schemes, drug design