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The University of Southampton

CHEM6148 Synthesis of Natural Products and Pharmaceuticals

Module Overview

Aims and Objectives

Learning Outcomes

Learning Outcomes

Having successfully completed this module you will be able to:

  • Understand the concept of retrons, and be able to recognise or introduce Diels-Alder and aldol retrons in target molecules
  • Understand other advanced retrosynthesis principles (e.g. key disconnection, chiral pool starting materials, reactive functional group, recognising symmetry)
  • Apply a retrosynthetic analysis that includes stereochemical aspects (identify suitable stereoselective strategies such as: resolution, chiral auxiliaries, enantioselective catalysis, enantiomerically pure starting material)
  • Understand key principles behind enantio- and diastereoselectivity, and develop skills to establish how the stereochemical outcome of reactions can be predicted
  • Demonstrate your understanding of the principles behind enantioselective synthesis
  • Problems of an unfamiliar nature are tackled with appropriate methodology and taking into account the possible absence of complete data.


The syllabus, which is outlined below, is aligned with the following QAA benchmark statements for chemistry at FHEQ Level 7 (Masters). • 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; • To extend their knowledge base to provide 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. 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 developed around a key concept, which is explained in detail and illustrated through the synthetic example. In addition, some concepts seen in earlier modules, such as retrosynthetic analysis, will be expanded to include stereochemical aspects and strategic disconnections. This is a course for students who are interested to pursue a career in synthetic organic chemistry (including all areas involving molecular synthesis. Some examples are: process development chemistry, medicinal chemistry, agrochemistry, fine chemicals and so on). Emphasis will be placed on developing the skills to identify and apply diastereoselective and enantioselective reactions to build chiral target molecules. Examples include drugs currently on the market (e.g. statins, HIV protease inhibitors, paroxetine) as well as natural products (monensin, hirsuten, etc) with important biological activities. 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 include: Diels-Alder reaction, alkylation and aldol reactions controlled by Evans auxiliaries, enamine and imine organocatalysis, Sharpless asymmetric epoxidation and dihydroxylation, allylic strain, and Felkin-Ahn models

Learning and Teaching

Teaching and learning methods

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

Preparation for scheduled sessions12
Follow-up work66
Problem Classes8
Total study time150



MethodPercentage contribution
Examination  (2 hours) 100%


MethodPercentage contribution
Examination  (2 hours) 100%

Repeat Information

Repeat type: Internal & External

Linked modules

CHEM3041 and (CHEM3038 or CHEM6095)

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