Professor Robin Giles

Room: PhSc/3.018

Research

Organic Chemical Synthesis and Structure Determination. The Synthesis of Compounds Containing Aromatic, Quinonoid and Heterocyclic Ring Systems. The Stereoselective and Enantioselective Synthesis of Compounds of Potential Medicinal or Biological Importance.

Projects

Compounds of Potential Medicinal Value

Various compounds from the quinone group have been shown to possess important properties which have been used exclusively in the treatment of severe medical ailments such as cancers and tuberculosis. Some of the first group that are currently in clinical use have some unpleasant side effects. A search for new compounds which are less toxic is under way.

The Synthesis of naphthopyranquinones

A number of naturally occurring naphthopyranquinones have recently been identified, and their structures partly assigned on the basis of spectroscopic evidence, but the structures could not be completely determined by such techniques. Many of these compounds show antibiotic activity.

We have recently synthesized some of these compounds in order to complete their identification; now that the basic route to this group of molecules has been established, it is intended to use this knowledge to assemble others in order to unambiguously assign the structures of the natural products.

The Stereoselective Isomerisation of aryldioxolanes into benzo-and naphthopyrans

We have shown that the isomerisation of aryldioxolanes is an effective method for the formation of benzo-and naphthopyrans, which occur widely in nature. Optimised routes to starting materials and their conversion to products are being investigated.

Synthesis of the Wilting Factors marticin and isomarticin

The plant pathogin Fusarium martii elaborates a group of quinones which act as wilting agents, chief amongst these being the benzoisochromanquinones marticin and isomarticin. Structures have been proposed for these compounds based on their spectroscopic data. While there is little doubt about the gross structures, there has been some controversy about regio- and stereochemical details. These compounds need to have their structures confirmed by synthesis.

Metal-catalysed stereoselective cyclisations

The enantioselective cyclisations of phenolic aldehydes to form 4,5-dihydroxyisochromans has been achieved. The generality of this reaction is being investigated.

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