Lewis Research Group

Synthetic Methodology & Natural Product Synthesis

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Research Aims

 

1.) Microbial Oxidation of Aromatic Rings

 

We are interested in the use of bacteria to carry out the dihydroxylation of aromatic rings—a process that would be very difficult to do by conventional chemical means. Of the arene dihydrodiol-producing organisms identified or engineered to date, the majority metabolise substituted arenes 1 to dihydrodiols with the 2,3 substitution pattern 2. An alternative outcome is the formation of 1,2-substituted dihydrodiols 3.

 

 

 

 

 

 

 

 

We are exploiting the microbial oxidation of benzoic acid, to produce 4 - a highly versatile chiral building block for synthesis

 

 

 

 

 

 

 

 

 

 

 

 

2.) Natural Product Total Synthesis

 

Our group is interested in total synthesis and we have used building block 4 to access natural products such as (+)-zeylenone 5 and (-)-grandifloracin 6. Separately, we also have a programme developing total syntheses of alkaloids of the lycopodium class.

 

 

 

 

 

 

 

 

 

 

3.) Metal-diene complexes

 

Bioproduct 4 and its derivatives have a rich organometallic chemistry and we have synthesized and characterized complexes of such dienes as iron carbonyls, cobalt cyclopentadienyls, etc. These complexes in turn allow access to a wider array of organic transformations of the cyclohexadiene, for example access to the opposite enantiomeric series of arene diols.

 

 

 

 

 

 

 

 

 

 

 

 

 

3.) Carbohydrate Chemistry

 

Chiron 4 is ideally functionalized for the synthesis of highly oxygenated structures such as carbohydrates. We recently reported access to a new class of hybrid inositol-amino acid structures, which we termed “inosamino acids”.

 

 

 

 

 

 

 

 

 

4.) C-H Activation with base metals

 

We are interested in using cheap, abundant metals such aluminium and iron to mediate the C-H activation of bulk hydrocarbons. Over 50 years ago, Baddeley reported an unusual “aliphatic Friedel-Crafts” acylation of decalin, which we have exploited to access a range of functionalized decalins. We are also currently probing the mechanism of this intriguing transformation.

 

 

 

 

 

 

 

 

 

 

5.) Dye-Sensitised Solar Cells

 

We are involved in a collaborative effort (with Dr Petra Cameron and Dr Matthew Jones) to develop new dye-sensitized solar cells which will be significant cheaper than the most well-known current examples. Many of the most efficient cells use ruthenium complexes as dyes, which presents a drawback in terms of cost. Accordingly, we are seeking to develop dyes that employ much cheaper metals but which have comparable cell characteristics.

 

6.) Other areas

 

We have recently initiated new projects in the areas of azulene chemistry and phosphine ligand design. We also have several other active collaborations on areas such as nociception.