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Details of Grant 

EPSRC Reference: GR/M93284/01
Title: APPLICATIONS OF 5-ENDO CYCLIZATIONS IN TARGET SYNTHESIS
Principal Investigator: Knight, Professor D
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Chemistry
Organisation: Cardiff University
Scheme: Standard Research (Pre-FEC)
Starts: 06 March 2000 Ends: 05 December 2003 Value (£): 163,463
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
Chemicals Pharmaceuticals and Biotechnology
No relevance to Underpinning Sectors
Related Grants:
Panel History:  
Summary on Grant Application Form
Initial studies will be focussed on the application of the recently discovered 5-endo-trig and -dig cyclisations of homoallylic and homopropargylic sulphonamides to the synthesis of highly substituted prolines. Thus far, such cyclisations have proven to be highly stereoselective, delivering different isomers, depending on the conditions. The major objectives in this section are to determine their characteristics when applied to the synthesis of highly substituted products and the best method to produce these in homochiral forms.These results will then be used to design total syntheses of members of the Cylindricine and Stenine families of natural products. The first group will feature extension of the model work to include spiro-pyrrolidine synthesis, which is expected to proceed with high levels of stereocontrol. The key steps in the projected Stenine syntheses are firstly 5-endo cyclisations followed by a second cyclisation, which will either be a 5-exo radical process or, in the case of the pyrrole-based targets, a Heck cyclisation. Much of this work, which is all aimed accessing homochiral products, will focus on methods for achieving stereocontrol during these key cyclisation steps.
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Organisation Website: http://www.cf.ac.uk