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Details of Grant 

EPSRC Reference: GR/T18240/01
Title: Evaluation of a Novel Approach Towards the Synthesis of Sarain A
Principal Investigator: Coldham, Professor I
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Chemistry
Organisation: University of Sheffield
Scheme: Standard Research (Pre-FEC)
Starts: 04 January 2005 Ends: 03 July 2006 Value (£): 88,501
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
Pharmaceuticals and Biotechnology Chemicals
Related Grants:
Panel History:  
Summary on Grant Application Form
The research described in this proposal involves synthetic organic chemistry. It aims to investigate a novel route for the preparation of the ring system present in a class of natural products called the sarain alkaloids. The sarains were isolated from a marine sponge from the Mediterranean Sea and have a unique structure and interesting biological properties, including anticancer, antibacterial and insecticidal activity.So far, four research groups in the USA have reported their efforts towards the preparation of the core ring system present in these natural products. These published routes are very lengthy and will hinder their use as methods to prepare the natural products or analogues for further biological evaluation.We propose a new, efficient route for the preparation of the core ring system, involving an intramolecular cydoaddition reaction of an azomethine ylide. We wish to test this hypothesis in a preliminary study to assess its feasibility. The cycloaddition has good precedent and the required ylides could be accessed either from aldehyde or oxazole precursors. We therefore need to prepare such precursors and to test their ability to undergo cycloaddition to give the required ring system that forms the core of the natural products.
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Organisation Website: http://www.shef.ac.uk