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EPSRC Reference: GR/M28439/01
Title: ON THE SYNTHESIS AND BIOSYNTHESIS OF PEYSSONOL A AND B: TWO HIV RTS INHIBITORS FROM A RED SEA ALGA
Principal Investigator: Harrowven, Professor DC
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Sch of Chemistry
Organisation: University of Southampton
Scheme: Standard Research (Pre-FEC)
Starts: 01 October 1999 Ends: 30 September 2002 Value (£): 54,495
EPSRC Research Topic Classifications:
Biological & Medicinal Chem.
EPSRC Industrial Sector Classifications:
Chemicals Pharmaceuticals and Biotechnology
No relevance to Underpinning Sectors
Related Grants:
Panel History:  
Summary on Grant Application Form
Peyssonol A and B, isolated from the Red Sea alga Peyssonnelia sp., are potent inhibitors of HIV reverse transcriptases. Their structures were determined by NMR studies but, due to limited bio-availability, an unequivocal assignment of the stereogenic centres in peyssonol B could not be established.The programme seeks to effect the total synthesis of both targets. Key steps envisioned for constructing the carbocyclic framework of peyssonol A in a stereo-controlled manner include a Michael initiated anion oxy-Cope rearrangement and a stepwise intramolecular Heck - conjugate addition sequence.At this juncture a trans-diaxial ring opening of an epoxide will be used to install the axial bromine in peyssonol A and the biomimetric skeletal rearrangement studied. The tow syntheses will be completed, allowing us to comment on the stereochemistry and biosynthesis of peyssonol B.
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Organisation Website: http://www.soton.ac.uk