The University of Southampton
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CHEM6108 Synthesis of Natural Products and Pharmaceuticals

Module Overview

This is a course for students who are interested to pursue a career in synthetic organic chemistry (including process chemistry, medicinal chemistry, synthetic biochemistry etc) and covers both natural product synthesis and the synthetic biochemistry.

Aims and Objectives

Module Aims

The aims of the module are: • to extend students' comprehension of key chemical concepts and so provide them with an in-depth understanding of specialised areas of chemistry; • to develop in students the ability to adapt and apply methodology to the solution of unfamiliar types of problems; • to instill a critical awareness of advances at the forefront of the chemical science discipline; • to prepare students effectively for professional employment or doctoral studies in the chemical sciences; • the ability to adapt and apply methodology to the solution of unfamiliar problems; • knowledge base extends to a systematic understanding and critical awareness of topics which are informed by the forefront of the discipline; • problems of an unfamiliar nature are tackled with appropriate methodology and taking into account the possible absence of complete data. Objectives: This is a research-led module and the lectures cover the synthesis of a selection of natural products and pharmaceuticals. Each of the examples is based on a certain concept, which is explained in detail and illustrated in the synthesis example. In addition, some concepts seen earlier, such as retrosynthetic analysis will be expanded. This is a course for students who are interested to pursue a career in synthetic organic chemistry (including process chemistry, medicinal chemistry, synthetic biochemistry etc). The emphasis will be on learning how diastereoselective and enantioselective reactions are used to build up chiral target molecules. Examples include drugs currently on the market (eg statins, HIV protease inhibitors, ) as well as natural products with promising biological activity.

Learning Outcomes

Learning Outcomes

Having successfully completed this module you will be able to:

  • Understand the concept or retrons, and be able to recognise or introduce Diels-Alder and aldol retrons in target molecules
  • Understand other advanced retrosynthesis principles (eg key disconnection, chiral pool, reactive functional group, recognising symmetry)
  • Apply a retrosynthetic analysis that includes stereochemical aspects (ability to derive which catalyst enantiomer is needed to achieve a particular stereochemistry)
  • understand the principles behind enantio- and diastereoselectivity, and analyse how the stereochemical outcome of reactions can be predicted;
  • demonstrate your understanding of the principles behind enantioselective synthesis;
  • Understand macrocyclisation strategies
  • know how to effect a number of important transformations, including Diels-Alder reactions, alkylations and aldol reactions using the Evans auxiliary, enantioselectivity through organocatalysis, diastereoselectivity using allylic strain.

Syllabus

The syllabus, which is described in outline below, is aligned with the following QAA benchmark statements for chemistry at FHEQ Level 7 (Masters). A focus is on investigating transition states to explain transfer of chirality, in a synthetic setting. It includes chiral auxiliaries, chiral catalysts, as well as simply starting from the chiral pool. Examples covered: beta-hydroxy ketone reduction, Diels-Alder reaction, alkylation, aldol reactions controlled by Evans auxiliaries, carbonyl affitions controlled by Felkin-Anh selectivity, and enamine and imine organocatalysis.

Learning and Teaching

Teaching and learning methods

Teaching methods: Lectures, directed reading, Blackboard online support. Learning methods: Independent study, student motivated peer group study

TypeHours
Lecture12
Practical classes and workshops4
Preparation for scheduled sessions6
Revision20
Follow-up work33
Total study time75

Resources & Reading list

Rios-Torres. Stereoselective organicatalysis. 

Clayden, Greeves, Warren. Organic Chemistry. 

Original chemical literature. 

Assessment

Summative

MethodPercentage contribution
Assessment  (1 hours) 100%

Referral

MethodPercentage contribution
Assessment  (1 hours) 100%

Linked modules

Pre-requisites: CHEM3038 and CHEM3041

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