Department of Chemistry

simon_lewis

Senior Lecturer

1 South 0.20

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

Tel: +44 (0) 1225 386568 

Personal website

 

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

Johnson, A., Pering, S., Deng, W., Troughton, J. R., Kubiak, P., Ghosh, D., Niemann, R., Brivio, F., Jeffrey, F., Walker, A., Islam, M., Watson, T., Raithby, P., Lewis, S. and Cameron, P., 2017. Azetidinium lead iodide for perovskite solar cells. Journal of Materials Chemistry A

Gee, A., Cosham, S. D., Johnson, A. L. and Lewis, S. E., 2017. Phosphorus-substituted azulenes accessed via direct hafner reaction of a phosphino cyclopentadienide. Synlett

Wills, K., Mandujano-Ramirez, H., Merino, G., Oskam, G., Cowper, P., Jones, M., Cameron, P. and Lewis, S., 2016. What difference does a thiophene make? Evaluation of a 4,4′-bis(thiophene) functionalised 2,2′-bipyridyl copper(I) complex in a dye-sensitized solar cell. Dyes and Pigments, 134, pp. 419-426.

Hazell, G., Gee, A. P., Arnold, T., Edler, K. J. and Lewis, S. E., 2016. Langmuir monolayers composed of single and double tail sulfobetaine lipids. Journal of Colloid and Interface Science, 474, pp. 190-198.

Lewis, S., 2016. Asymmetric Dearomatization Under Enzymatic Conditions. In: You, S.-L., ed. Asymmetric Dearomatization Reactions. Wiley, pp. 279-346.

Cowper, P., Jin, Y., Turton, M. D., Kociok-Kohn, G. and Lewis, S. E., 2016. Azulenesulfonium salts:accessible, stable, and versatile reagents for cross-coupling. Angewandte Chemie-International Edition, 55 (7), pp. 2564-2568.

Ten Broeke, M., Ali Khan, M., Kociok-Kohn, G., Kann, N. and Lewis, S. E., 2015. Tricarbonyliron(0) complexes of bio-derived η4 cyclohexadiene ligands: An approach to analogues of oseltamivir. Journal of Organometallic Chemistry, 799-800, pp. 19-29.

Lewis, S., 2015. Biotransformations of Arenes:An Overview. In: Mortier, J., ed. Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds. Wiley, pp. 913-937.

Lewis, S. E., 2015. Cycloparaphenylenes and related nanohoops. Chemical Society Reviews, 44 (8), pp. 2221-2304.

Lyall, C. L., Shotton, C. C., Pérez-salvia, M., Pantos, D. and Lewis, S. E., 2014. Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation. Chemical Communications, 50 (89), pp. 13837-13840.

Lyall, C.L., Sato, M., Uosis-Martin, M., Asghar, S.F., Jones, M., Williams, I.H. and Lewis, S., 2014. C-H functionalization of sp3 centers with Aluminum:A computational and mechanistic study of the baddeley reaction of Decalin. Journal of the American Chemical Society, 136 (39), pp. 13745-13753.

Laabei, M., Jamieson, W. D., Lewis, S. E., Diggle, S. P. and Jenkins, A. T. A., 2014. A new assay for rhamnolipid detection-important virulence factors of Pseudomonas aeruginosa. Applied Microbiology and Biotechnology, 98 (16), pp. 7199-7209.

Ali Khan, M., Wood, P. J., Lamb-Guhren, N. M., Caggiano, L., Kociok-Köhn, G., Tosh, D. and Lewis, S. E., 2014. The enone motif of (+)-grandifloracin is not essential for 'anti-austerity' antiproliferative activity. Bioorganic & Medicinal Chemistry Letters, 24 (13), pp. 2815-2819.

Lewis, S. E., 2014. Applications of biocatalytic arene ipso,ortho cis-dihydroxylation in synthesis. Chemical Communications, 50 (22), pp. 2821-2830.

Griffen, J. A., Kenwright, S. J., Abou-shehada, S., Wharry, S., Moody, T. S. and Lewis, S. E., 2014. Benzoate dioxygenase from Ralstonia eutropha B9 – unusual regiochemistry of dihydroxylation permits rapid access to novel chirons. Organic Chemistry Frontiers, 1 (1), pp. 79-90.

Wills, K. A., Mandujano-ramírez, H. J., Merino, G., Mattia, D., Hewat, T., Robertson, N., Oskam, G., Jones, M. D., Lewis, S. E. and Cameron, P. J., 2013. Investigation of a copper(i) biquinoline complex for application in dye-sensitized solar cells. RSC Advances, 3 (45), pp. 23361-23369.

Griffen, J., White, J., Kociok-Kohn, G., Lloyd, M., Wells, A., Arnot, T. and Lewis, S., 2013. New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho-arene dihydrodiol. Tetrahedron, 69 (29), pp. 5989-5997.

Lyall, C., Uosis-Martin, M., Lowe, J., Mahon, M. F., Pantos, G. D. and Lewis, S. E., 2013. Aliphatic C–H activation with aluminium trichloride–acetyl chloride:Expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons. Organic and Biomolecular Chemistry, 11 (9), pp. 1468-1475.

Uosis-Martin, M., Pantos, G. D., Mahon, M. F. and Lewis, S. E., 2013. A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition. Journal of Organic Chemistry, 78 (12), pp. 6253-6263.

Ali Khan, M., Mahon, M. F., Lowe, J. P., Stewart, A. J. W. and Lewis, S. E., 2012. Valuable new cyclohexadiene building blocks from cationic η5-iron-carbonyl complexes derived from a microbial arene oxidation product. Chemistry - A European Journal, 18 (42), pp. 13480-13493.

Palframan, M. J., Kociok-Kohn, G. and Lewis, S. E., 2012. Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLamare rearrangement: Total synthesis of zeylenols and zeylenones. Chemistry - A European Journal, 18 (15), pp. 4766-4774.

Van Der Waals, D., Pugh, T., Khan, M. A., Stewart, A. J. W., Johnson, A. L. and Lewis, S. E., 2011. A cobalt complex of a microbial arene oxidation product. Chemistry Central Journal, 5 (1), 80.

Andersson, D. A., Gentry, C., Alenmyr, L., Killander, D., Lewis, S. E., Andersson, A., Bucher, B., Galzi, J. L., Sterner, O., Bevan, S., Hogestatt, E. D. and Zygmunt, P. M., 2011. TRPA1 mediates spinal antinociception induced by acetaminophen and the cannabinoid Δ9-tetrahydrocannabiorcol. Nature Communications, 2, 551.

Uosis-Martin, M., Mahon, M. F., Jevglevskis, M. and Lewis, S. E., 2011. Concise Synthesis of 1,4a-Bifunctionalised Decalin Building Blocks by C-H Activation of Decalin. Synlett, 2011 (15), pp. 2211-2213.

Palframan, M. J., Kociok-Kohn, G. and Lewis, S. E., 2011. Total synthesis of (+)-grandifloracin by iron complexation of a microbial arene oxidation product. Organic Letters, 13 (12), pp. 3150-3153.

Griffen, J. A., Le Coz, A. M., Kociok-Kohn, G., Ali Khan, M., Stewart, A. J. W. and Lewis, S. E., 2011. Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds. Organic and Biomolecular Chemistry, 9 (10), pp. 3920-3928.

Pilgrim, S., Kociok-Kohn, G., Lloyd, M. D. and Lewis, S. E., 2011. "Inosaminoacids": novel inositol-amino acid hybrid structures accessed by microbial arene oxidation. Chemical Communications, 47 (16), pp. 4799-4801.

Ali Khan, M., Lowe, J. P., Johnson, A. L., Stewart, A. J. W. and Lewis, S. E., 2011. Accessing the antipodal series in microbial arene oxidation: a novel diene rearrangement induced by tricarbonyliron(0) complexation. Chemical Communications, 47 (1), pp. 215-217.

Baker, T. and Lewis, S. E., 2010. Bifunctional silyl triflates in synthesis. Part 1: Synthesis and characterization of novel alkane-,-diyl-bis(silyl triflates). Synthetic Communications, 40 (18), pp. 2747-2752.

Craig, D., Gore, S. J., Lansdell, M. I., Lewis, S., Mayweg, A. V. W. and White, A. J. P., 2010. Transannular, decarboxylative Claisen rearrangement reactions for the synthesis of sulfur-substituted vinylcyclopropanes. Chemical Communications, 46 (27), pp. 4991-4993.

Lewis, S. E., 2010. Synthetic methods: part (ii) oxidation and reduction methods. Annual Reports - Section B Organic Chemistry, 106, pp. 34-75.

Kociok-Kohn, G. and Lewis, S., 2010. Crystallographic rationalization of the reactivity and spectroscopic properties of (2R)-S-(2,5-dihydroxyphenyl)cysteine. Acta Crystallographica Section C-Crystal Structure Communications, 66 (4), O187-O189.

Ali Khan, M., Mahon, M. F., Stewart, A. J. W. and Lewis, S. E., 2010. Iron(0) tricarbonyl complexes of microbially derived cyclohexadiene ligands containing quaternary stereocenters. Organometallics, 29 (1), pp. 199-204.

Lewis, S. E., 2009. Synthetic methods:part (ii) oxidation and reduction methods. Annual Reports - Section B Organic Chemistry, 105, pp. 35-74.

This list was generated on Tue Oct 17 12:14:41 2017 IST.

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