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Details of Grant 

EPSRC Reference: GR/R20465/01
Title: A New Approach To the Synthesis of Breynolide
Principal Investigator: Grainger, Dr RS
Other Investigators:
Researcher Co-Investigators:
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Department: Chemistry
Organisation: Kings College London
Scheme: Fast Stream
Starts: 01 July 2001 Ends: 30 June 2004 Value (£): 63,833
EPSRC Research Topic Classifications:
Asymmetric Chemistry Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
Pharmaceuticals and Biotechnology
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Summary on Grant Application Form
This project seeks to develop new methods of preparing the key structural features of the sulfur-containing antibiotic breynolide. Application of the rich organic chemistry associated with sulfur is the key to the synthesis of the left-hand portion of the molecule. A new means of stereoselective synthesis is proposed based on a symmetry breaking cycloaddition reaction of a sulfenic acid with an alkene. A study on the nature of this reaction using different alkenes will increase our fundamental knowledge of the system. The sulfoxide group formed as a consequence of this cyclisation will De used to further aid in the synthesis of more complicated derivatives. A model for the right hand portion of breynolide will be synthesised in a small number of synthetic steps using a photochemical ring closing reaction, which dramatically increases molecular complexity. A combination of these IWO new strategies will be applied to the synthesis of simple model compounds related to breynolide, which may also display significant biological activity.
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