Department of Chemistry

simon_lewis

Senior Lecturer

1 South 0.20

Email: S.E.Lewis@bath.ac.uk

Tel: +44 (0) 1225 386568 

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Dr Simon Lewis

Profile

Microbial Oxidation of Aromatic Rings

We are interested in using bacteria to carry out dihydroxylation of aromatic rings—a process that is very difficult by conventional chemical means. Of the strains identified or engineered to date, the majority metabolise substituted arenes to dihydrodiols with the ortho,meta-substitution pattern.  Much rarer is the formation of ipso,ortho-substituted dihydrodiols.  We are exploiting the microbial ipso,ortho-dihydroxylation of benzoic acid, producing a versatile chiral building block for synthesis.

Natural Product Total Synthesis

We are working on two target classes.  Firstly, polyoxygenated cyclohexenes of the zeylenol and zeylenone families are accessible from the dihydrodiols described above and we have completed syntheses of many such natural products.  Of these, Grandifloracin is of particular interest as it displays "anti-austerity" activity against pancreatic cancer cells.  Secondly, we are interested in lycopodium alkaloids e.g. complanadines accessing these by Kondrat'eva oxazole-olefin cycloaddition.

Metal-diene complexes

Arene cis-diols have rich organometallic chemistry and we have synthesised complexes of such dienes as iron carbonyls, cobalt cyclopentadienyls, etc.  These allow access to a wider array of transformations of the cyclohexadiene, for example access to the opposite enantiomeric series of arene dihydrodiols. 

Carbohydrates

Arene cis-diols are also ideally functionalised for 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 "inosaminoacids".

C-H Activation with base metals

We are using aluminium and iron - cheap, abundant metals - for C-H activation of bulk hydrocarbons.  Over 50 years ago, Baddeley reported an “aliphatic Friedel-Crafts” acylation of decalin, which we exploit to access a range of functionalised decalins. We are probing the mechanism of this intriguing transformation.

Dye-Sensitized Solar Cells

We have projects on the synthesis of new dyes for use in solar cell applications, both metal complexes and purely organic dyes.

Publications

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