Research

New strategies for asymmetric synthesis

The development of new strategies for controlling stereochemistry

Our synthetic chemistry research is not centred around a particular reaction or functional group.  Instead, we strive to develop new synthetic strategies which are widely applicable in the synthesis of biologically active compounds.  We are particularly interested in the development of new strategies for controlling stereochemistry.  There are many hundreds of examples of desymmetrisation of molecules with an internal mirror plane.  However, the approach can be applied to the desymmetrisation of molecules with any improper element of symmetry.  We have applied a wide range of asymmetric reactions to the desymmetrisation of centrosymmetric molecules including epoxide and ester hydrolyses, aldol reactions and amide formations.  We have exploited the approach for the first time in natural product synthesis: in the preparation of an intermediate in a total synthesis of Hemibrevetoxin B, and in the total synthesis of the alkaloid, Dragmacidin B.

Publications in this area:

65 Karen  Dodd , Daniel  Morton , Robert  Narquizian, Adam  Nelson and Stephen  Worden , "Desymmetrisation of a Centrosymmetric Molecule by Carbon-Carbon Bond Formation: Asymmetric Aldol Reactions of a Centrosymmetric Dialdehyde", Chem. Eur. J. 2007, 13, 5857-5861
Open Access Version
Keywords: "New strategies for asymmetric synthesis"

60 Mark  Anstiss and Adam  Nelson , "Catalytic and stoichiometric approaches to the desymmetrisation of centrosymmetric piperazines by enantioselective acylation: A total synthesis of Dragmacidin A", Org. Biomol. Chem. 2006, 4, 4135-4143
Open Access Version - provided courtesy of the RSC
Keywords: "New strategies for asymmetric synthesis" "Natural product synthesis"

53 Andrew  Kennedy , Adam  Nelson and Alexis  Perry , "Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: Exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives", Beilstein J. Org. Chem. 2005, 1, 2
Keywords: "Stereochemically diverse libraries" "New strategies for asymmetric synthesis"

48 Alan  Ironmonger , Adam  Nelson and Peter  Stockley, "Asymmetric double ring-opening of a C2h-symmetric bisepoxide: Improved enantiomeric excess of the product through enantioselective desymmetrisation and ‘proof-reading’ steps", Org. Biomol. Chem. 2005, 3, 2350-2353
Open Access Version - provided courtesy of the RSC
Keywords: "New strategies for asymmetric synthesis"

42 Adam  Nelson , "The development of strategies and methods for the synthesis of biologically active compounds", New J. Chem. 2004, 28, 771-776
Open Access Version - provided courtesy of the RSC
Keywords: "Stereochemically diverse libraries" "New strategies for asymmetric synthesis" "Natural product synthesis"

35 Mark  Anstiss , Joanne  Holland , Adam  Nelson and James  Titchmarsh , "Beyond breaking the mirror plane: The desymmetrisation of centrosymmetric molecules as an efficient strategy for asymmetric synthesis", Synlett 2003, , 1213-1220
Keywords: "New strategies for asymmetric synthesis" "Natural product synthesis"

32 Joanne  Holland , Mark  Lewis and Adam  Nelson , "Desymmetrisation of a Centrosymmetric Diepoxide: Efficient Synthesis of a Key Intermediate in a Total Synthesis of Hemibrevetoxin B", J. Org. Chem. 2003, 68, 747-753
Keywords: "New strategies for asymmetric synthesis" "Natural product synthesis"

31 Steve  Bartlett , Robert  Hodgson , Joanne  Holland , Matthew  Jones , Colin  Kilner , Adam  Nelson and Stuart  Warriner , "Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals", Org. Biomol. Chem. 2003, 1, 2393-2402
Open Access Version - provided courtesy of the RSC
Keywords: "Stereochemically diverse libraries" "New strategies for asymmetric synthesis"

29 Michael  Harding , Robert  Hodgson , Tahir  Majid , Kenny  McDowall and Adam  Nelson , "A stereodivergent, two-directional synthesis of stereoisomeric C-linked disaccharide mimetics", Org. Biomol. Chem. 2003, 1, 338-349
Open Access Version - provided courtesy of the RSC
Keywords: "Stereochemically diverse libraries" "New strategies for asymmetric synthesis"

28 Michael  Harding , Robert  Hodgson and Adam  Nelson , "Sequential kinetic resolution of C2-symmetric compounds as a key step in two-directional synthesis: Structural requirements for efficient resolution of difuryl diols", J. Chem. Soc., Perkin Trans. 1 2002, , 2403-2413
Open Access Version - provided courtesy of the RSC
Keywords: "New strategies for asymmetric synthesis"

27 Robert  Hodgson , Tahir  Majid and Adam  Nelson , "Desymmetrisation of meso difuryl alcohols, diols and their derivatives: complementary directed and undirected asymmetric dihydroxylation reactions", J. Chem. Soc., Perkin Trans. 1 2002, , 1631-1643
Open Access Version - provided courtesy of the RSC
Keywords: "Stereochemically diverse libraries" "New strategies for asymmetric synthesis"

25 Joanne  Holland , Mark  Lewis and Adam  Nelson , "First desymmetrisation of a centrosymmetric molecule in natural product synthesis: Preparation of a key fragment in the synthesis of Hemibrevetoxin B", Angew. Chem., Int. Ed. 2001, 40, 4082-4084
Keywords: "New strategies for asymmetric synthesis" "Natural product synthesis"

24 Adam  Nelson , "Looking in the mirror", Chemistry Review 2001, 10, issue 3, 6-9
Keywords: "New strategies for asymmetric synthesis"

People currently working in this research area:

Adam Nelson

Alexandre Trindade