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Presentation Transcript

Lecture 1: 

Lecture 1 Retrosynthesis

Organic Synthesis: 

Organic Synthesis “The preparation of a desired organic compound from commercially available starting materials via some multi-step procedure” Used in: Pharmaceutical Agrochemicals Perfumes Dyes Polymers

Organic Synthesis: 

Organic Synthesis Q. Where do we start with complex molecules? A. Work backwards, starting from the product RETROSYNTHESIS

Retrosynthesis: 

Retrosynthesis “The analytical process of designing a synthetic route for the preparation of an organic compound from readily available starting materials.” Like a game of chess: Rules Learnable moves Underpinning strategies Practice makes Perfect!

How will the course be taught?: 

How will the course be taught? Lectures Workshops/Tutorials Online Resources Practice Questions Worked Examples Quizzes Revision Videos Revision Aids

Organic Synthesis: 

Organic Synthesis Learning Outcomes: Use retrosynthetic analysis to devise a strategy for the synthesis of a target molecule Propose a detailed synthetic route to the target molecule from readily available starting materials Recommended Texts: “Organic Synthesis. The Disconnection Approach”. S. Warren. Wiley; 1982. “Organic Synthesis”. M. Wills and C. Willis. Oxford Primer, OUP; 1995 “Organic Chemistry” Clayden, Greeves, Warren and Worthers. OUP; 2001.

Main considerations: 

Main considerations Construction of Carbon framework Requires good knowledge of C-C bond forming reactions Involves decisions about which bonds should be made Functional Group Interconversions (FGIs) Often require certain functional groups at certain stages in a synthesis E.g. Oxidation, Reduction, Hydrolysis Stereocontrol Often need to synthesise only one of a number of possible stereoisomers Only briefly touched on in this course

Retrosynthesis: 

Retrosynthesis Designing a synthetic route by taking one or more backwards, or retrosynthetic, steps Definitions: Target Molecule – the molecule to be prepared Disconnection – analytical operation of breaking a bond, the reverse of a chemical reaction, to produce 2 synthons Synthon – an imaginary idealised fragment, usually an ion, corresponding to nucleophilic or electrophilic species Synthetic Equivalent – a real reagent that is equivalent to a certain synthon Functional Group Interconversion (FGI) – the operation of replacing one functional group with another

Retrosynthesis: 

Retrosynthesis

Important Steps: 

Important Steps 1. Choosing the correct disconnection Corresponds to a reliable forward reaction  Make use of functional groups Gives significant simplification:  centre of molecule  branch points  symmetry Gives synthons with recognisable synthetic equivalents

Important Steps: 

Important Steps 2. Assigning the charges to the synthons Consider both synthon pair options Make use of latent polarity Must correspond to reactive and available synthetic equivalents Available to buy Can easily be prepared

ToolKit - Carbon Electrophiles: 

ToolKit - Carbon Electrophiles

Lecture 1: Summary: 

Lecture 1: Summary Introduction Main Considerations Definition of Terms Important Steps Carbon Electrophiles

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