The Sutherland Research Group: Publications

2012

S. Ahmad, M. D. Swift, L. J. Farrugia, H. M. Senn and A. Sutherland, Stereoselective Synthesis Of Functionalised Carbocyclic Amides; Construction Of The syn-(4aS,10bS)-Phenanthridone Skeleton, Org. Biomol. Chem., 2012, 10, 3937-3945.

A. A. Cant, R. Bhalla, S. L. Pimlott and A. Sutherland, Nickel-Catalysed Aromatic Finkelstein Reaction Of Aryl and Heteroaryl Bromides, Chem. Commun., 2012, 48, 3993-3995.

R. A. Hill and A. Sutherland, Hot off the Press, Nat. Prod. Rep., 2012, 29, 129-133, 435-439.


2011

A. Zaed and A. Sutherland, Total Synthesis Of Clavaminol A, C and H, Org. Biomol. Chem., 2011, 9, 8030-8037. Second top accessed article from OBC in August 2011 (as an advanced article). Article featured on the front cover of the journal.

M. Daly, K. Gill, M. Sime, G. L. Simpson and A. Sutherland, A New General Approach For The Stereocontrolled Synthesis Of Functionalised γ- and δ-lactams, Org. Biomol. Chem., 2011, 9, 6761-6770.

L. S. Fowler, L. H. Thomas, D. Ellis and A. Sutherland, A One-Pot, Reductive Amination/6-endo-trig Cyclisation For The Stereoselective Synthesis Of 6-Substituted-4-Oxopipecolic Acids, Chem. Commun., 2011, 47, 6569-6571.

S. Ahmad, L. H. Thomas and A. Sutherland, Stereoselective Synthesis Of Polyhydroxylated Aminocyclohexanes, Org. Biomol. Chem., 2011, 9, 2801-2808.

F. I. McGonagle, L. Brown, A. Cooke and A. Sutherland, Microwave-Promoted Tandem Reactions For The Synthesis Of Bicyclic γ-Lactams, Tetrahedron Lett., 2011, 52, 2330-2332.

A. A. S. Tavares, N. K. Jobson, D. Dewar, A. Sutherland and S. Pimlott, ¹²³I-NKJ64: A Novel SPECT Radiotracer For Imaging The Noradrenaline Transporter In Brain, Synapse, 2011, 65, 658-667.

L. S. Fowler and A. Sutherland, Product Class 6: Acyclic And Semicyclic O/O Acetals, In Science Of Synthesis Knowledge Updates, D. J. Procter, G. A. Molander, Eds.; Thieme: Stuttgart, 2011, Vol. 2010/3, Section 29.6.2, p 121-150.

A. A. S. Tavares, N. K. Jobson, D. Dewar, A. Sutherland and S. Pimlott, Development Of The Radiosynthesis Of High-Specific-Activity ¹²³I-NKJ64, Nucl. Med. Biol., 2011, 38, 493-500.

S. L. Pimlott and A. Sutherland, Molecular Tracers For The PET And SPECT Imaging Of Disease, Chem. Soc. Rev., 2011, 40, 149-162.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2011, 28, 182-185, 659-662, 1031-1034, 1345-1349, 1621-1625, 1879-1882. Top ten accessed articles from NPR in January, March, April and June 2011.


2010

A. R. Kennedy, W. J. Kerr, L. C. Paterson and A. Sutherland, A Tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one Of Defined Relative Stereochemistry For Use Towards Agariblazeispirol C, Acta Cryst., 2010, C66, o473-o474.

A. M. Zaed and A. Sutherland, Stereoselective Synthesis Of The Bicyclic Guanidine Alkaloid (+)-Monanchorin, Org. Biomol. Chem., 2010, 8, 4394-4399. Top ten accessed article from OBC in September 2010.

L. J. Drummond and A. Sutherland, Asymmetric Synthesis Of Allylic Secondary Alcohols: A New General Approach For The Preparation of α-Amino Acids, Tetrahedron, 2010, 66, 5349-5356.

F. I. McGonagle, L. Brown, A. Cooke and A. Sutherland, A Three-Step Tandem Process For The Synthesis Of Bicyclic γ-Lactams, Org. Biomol. Chem., 2010, 8, 3418-3425. Article featured on the front cover of the journal. Top ten accessed article from OBC in July 2010.

L. Stevenson, A. A. S. Tavares, A. Brunet, F. I. McGonagle, D. Dewar, S. L. Pimlott and A. Sutherland, New Iodinated Quinoline-2-Carboxamides For SPECT Imaging Of The Translocator Protein, Bioorg. Med. Chem. Lett., 2010, 20, 954-957.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2010, 27, 149-152, 477-480, 805-808, 1110-1113, 1381-1385, 1733-1736.


2009

L. S. Fowler, D. Ellis and A. Sutherland, Synthesis Of Fluorescent Enone Derived α-Amino Acids, Org. Biomol. Chem., 2009, 7, 4309-4316.

C. M. Reid and A. Sutherland, Synthesis Of Isotopically Labeled α-Amino Acids, Chapter 11 In Volume 1 Of Amino Acids, Peptides And Proteins In Organic Chemistry, Ed., A. B. Hughes, Wiley-VCH, Weinheim, 2009.

N. K. Jobson, A. R. Crawford, D. Dewar, S. L. Pimlott and A. Sutherland, Design And Synthesis Of (2R,3S)-Iodoreboxetine Analogues For SPECT Imaging Of The Noradrenaline Transporter, Bioorg. Med. Chem. Lett., 2009, 19, 4996-4998. SINAPSE paper of the month.

A. M. Zaed, M. D. Swift and A. Sutherland, A Stereoselective Synthesis Of (+)-Physoperuvine Using A Tandem Aza-Claisen Rearrangement And Ring Closing Metathesis Reaction, Org. Biomol. Chem., 2009, 7, 2678-2680. Article featured on the front cover of the journal.

M. D. Swift, A. Donaldson and A. Sutherland, Tandem Aza-Claisen Rearrangement And Ring Closing Metathesis Reactions: The Stereoselective Synthesis Of Functionalised Carbocyclic Amides, Tetrahedron Lett., 2009, 50, 3241-3244. Invited contribution to a special 50th anniversary issue.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2009, 26, 151-154, 461-464, 725-728, 973-976, 1229-1233, 1517-1520.


2008

C. M. Reid, C. Ebikeme, M. P. Barrett, E.-M. Patzewitz, S. Muller, D. J. Robins and A. Sutherland, Synthesis Of Novel Benzamidine- And Guanidine-Derived Polyazamacrocycles: Selective Anti-Protozoal Activity For Human African Trypanosomiasis, Bioorg. Med. Chem. Lett., 2008, 18, 5399-5401.

N. K. Jobson, A. R. Crawford, D. Dewar, S. L. Pimlott and A. Sutherland, New Iodoreboxetine Analogues For SPECT Imaging Of The Noradrenaline Transporter, Bioorg. Med. Chem. Lett., 2008, 18, 4940-4943.

M. D. Swift and A. Sutherland, Studies On The aza-Claisen Rearrangement of 4,5-Dihydroxylated Allylic Trichloroacetimidates: The Stereoselective Synthesis Of (2R,3S)- And (2S,3S)-2-Amino-3,4-Dihydroxybutyric Acids, Tetrahedron, 2008, 64, 9521-9527.

N. K. Jobson, R. Spike, A. R. Crawford, D. Dewar, S. L. Pimlott and A. Sutherland, Stereoselective Synthesis of (2S,3R)- and (2R,3S)-iodoreboxetine; Potential SPECT Imaging Agents For The Noradrenaline Transporter, Org. Biomol. Chem., 2008, 6, 2369-2376. Article featured in Chemical Biology, 2008, issue 8.

S. L. Pimlott, L. Stevenson, D. J. Wyper and A. Sutherland, Rapid And Efficient Radiosynthesis of [¹²³I]-I-PK11195, A SPECT Tracer For The Peripheral Benzodiazepine Receptors, Nucl. Med. Biol., 2008, 35, 537-542.

C. M. Reid, C. Ebikeme, M. P. Barrett, E.-M. Patzewitz, S. Muller, D. J. Robins and A. Sutherland, Synthesis And Anti-protozoal Activity Of C2-Substituted Polyazamacrocycles, Bioorg. Med. Chem. Lett., 2008, 18, 2455-2458.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2008, 25, 11-14, 216-219, 443-446, 647-650, 841-844, 997-1000.


2007

M. D. Swift and A. Sutherland, A Tandem Aza-Claisen Rearrangement And Ring Closing Metathesis Reaction For The Synthesis of Cyclic Allylic Trichloroacetamides, Org. Lett., 2007, 9, 5239-5242.

K. N. Fanning and A. Sutherland, A Facile Synthesis of (S)-Gizzerosine, A Potent Agonist Of The Histamine H2-Receptor, Tetrahedron Lett., 2007, 48, 8479-8481.

J. M. Wilson, F. Giordani, L. J. Farugia, M. P. Barrett, D. J. Robins and A. Sutherland, Synthesis, Characterisation and Anti-Protozoal Activity Of Carbamate-Derived Polyazamacrocycles, Org. Biomol. Chem., 2007, 5, 3651-3656.

B. Pillai, M. Cherney, C. M. Diaper, A. Sutherland, J. S. Blanchard, J. C. Vederas and M. N. G. James, Dynamics of Catalysis Revealed From Crystal Structures of Mutants of Diaminopimelate Epimerase, Biochem. Biophys. Res. Commun., 2007, 363, 547-553.

L. Stevenson, S. L. Pimlott and A. Sutherland, A Novel Approach For The Synthesis Of The Peripheral Benzodiazepine Receptor Ligand, PK11195, Tetrahedron Lett., 2007, 48, 7137-7139.

R. Bischoff, D. J. Hamilton, N. K. Jobson and A. Sutherland, New Approaches For The Synthesis Of Isotopically Labelled Guanidine-Derived Amino Acids and Noradrenaline Reuptake Inhibitors, J. Labelled Compds. Radiopharm., 2007, 50, 323-326.

M. D. Swift and A. Sutherland, A Stereoselective Synthesis of (2R,3S)-2-Amino-3,4-Dihydroxybutyric Acid Using An Ether Directed aza-Claisen Rearrangement, Tetrahedron Lett., 2007, 48, 3771-3773.

A. G. Jamieson and A. Sutherland, Ether-Directed, Stereoselective Aza-Claisen Rearrangements: Synthesis Of The Piperidine Alkaloid, α-Conhydrine, Org. Lett., 2007, 9, 1609-1611.

A. G. Jamieson and A. Sutherland, Ether-Directed Palladium(II)-Catalysed Aza-Claisen Rearrangements: Studies On The Origin Of The Directing Effect, Tetrahedron, 2007, 63, 2123-2131.

J. M. Wilson, G. Henderson, F. Black, A. Sutherland, R. L. Ludwig, K. H. Vousden and D. J. Robins, Synthesis of 5-Deazaflavin Derivatives And Their Activation Of p53 in Cells, Bioorg. Med. Chem., 2007, 15, 77-86.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2007, 24, 14-17, 263-266, 500-503, 655-658, 927-930, 1207-1210.


2006

M. D. Swift and A. Sutherland, Stereocontrol Of Palladium(II)-Catalysed aza-Claisen Rearrangements Using A Combination Of 1,3-Allylic Strain And A Solvent Mediated Directing Effect, Org. Biomol. Chem., 2006, 4, 3889-3891.

A. G. Jamieson and A. Sutherland, Scope And Limitations Of Ether-Directed, Metal-Catalysed aza-Claisen Rearrangements; Improved Stereoselectivity Using Non-coordinating Solvents, Org. Biomol. Chem., 2006, 4, 2932-2937.

B. Pillai, M. M. Cherney, C. M. Diaper, A. Sutherland, J. S. Blanchard, J. C. Vederas and M. N. G. James, Structural Insights Into Stereochemical Inversion By Diaminopimelate Epimerase: An Antibacterial Drug Target, Proc. Natl. Acad. Sci. USA, 2006, 103, 8668-8673.

K. N. Fanning, A. G. Jamieson and A. Sutherland, Palladium(II)-Catalysed Rearrangement Reactions, Curr. Org. Chem., 2006, 10, 1007-1020.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2006, 23, 11-14, 143-146, 343-346, 513-516, 669-672, 841-844.

2005

C. M. Diaper, A. Sutherland, B. Pillai, M. N. G. James, P. Semchuk, J. S. Blanchard and J. C. Vederas, The Stereoselective Synthesis Of Aziridine Analogues Of Diaminopimelic Acid (DAP) And Their Interaction With DAP Epimerase, Org. Biomol. Chem., 2005, 3, 4402-4411. Article featured on the front cover of the journal.

K. N. Fanning, A. G. Jamieson and A. Sutherland, Stereoselective β-Hydroxy-α-Amino Acid Synthesis Via An Ether Directed, Palladium Catalysed, aza-Claisen Rearrangement, Org. Biomol. Chem., 2005, 3, 3749-3756.

R. Bischoff, N. McDonald and A. Sutherland, A Highly Efficient, Asymmetric Synthesis Of Blastidic Acid: The β-Amino Acid Component Of The Antibiotic, (+)-Blasticidin S, Tetrahedron Lett., 2005, 46, 7147-7149.

A. G. Jamieson and A. Sutherland, A Highly Stereoselective Ether Directed Palladium Catalysed Aza-Claisen Rearrangement, Org. Biomol. Chem., 2005, 3, 735-736.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2005, 22, 11-14, 141-143, 320-323, 436-438, 559-562, 668-671.

D. J. Hamilton and A. Sutherland, A Flexible Approach For The Synthesis Of Selectively Labelled L-Arginine, Tetrahedron Lett., 2004, 45, 5739-5741.

A. G. Jamieson, A. Sutherland and C. L. Willis, The First Enantioselective Synthesis Of The Amino Acid, (2S,3S,4R)-γ-hydroxyisoleucine Using a Palladium(II) Catalysed 3,3-Sigmatropic Rearrangement, Org. Biomol. Chem., 2004, 2, 808-809.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2004, 21, H1-H4, H5-H8, H9-H12, H13-H15, H17-H21, H23-H26.


2003

G. Karig, J. M. Large, C. G. V. Sharples, A. Sutherland, T. Gallagher and S. Wonnacott, Synthesis and Nicotinic Binding Of Novel Phenyl Derivatives Of UB-165. Identifying Factors Associated with α-7 Selectivity, Bioorg. Med. Chem. Lett., 2003, 13, 2825-2828.

A. Sutherland and T. Gallagher, The Synthesis And Reactivity Of Halopyridylboronic Acids, Reactivity, 2003, 4-7.

A. Sutherland and T. Gallagher, Versatile Synthesis Of 3,5-Disubstituted 2-Fluoropyridines And 2-Pyridones, J. Org. Chem., 2003, 68, 3352-3355.

A. Sutherland, T. Gallagher, C. G. V. Sharples and S. Wonnacott; The Synthesis Of Two Fluoro Analogues Of The Nicotinic Acetylcholine Receptor Agonist UB-165, J. Org. Chem., 2003, 68, 2475-2478.

R. A. Hill and A. Sutherland, Hot Off The Press, Nat. Prod. Rep., 2003, 20, xlv-xlviii.
 

2002

A. Sutherland and J. C. Vederas, Conjugate Addition Of Radicals Generated From Diacyloxyiodobenzenes to Dehydroamino Acid Derivatives; A Synthesis of Diaminopimelic Acid Analogues, Chem. Commun., 2002, 224-225.


2001 

J. F. Caplan, A. Sutherland and J. C. Vederas, The First Stereospecific Synthesis of L-Tetrahydrodipicolinic Acid; A Key Intermediate Of Diaminopimelate Metabolism, J. Chem. Soc., Perkin Trans. 1, 2001, 2217-2220.
 
A. Sutherland, K. Auclair and J. C. Vederas, Recent Advances In The Biosynthetic Studies Of Lovastatin, Current Opinion in Drug Discovery and Development, 2001, 4, 229-236.
 

2000

K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson and J. C. Vederas, Lovastatin Nonaketide Synthase Catalyses An Intramolecular Diels-Alder Reaction Of A Substrate Analogue, J. Am. Chem. Soc., 2000, 122, 11519-11520.
 
A. Sutherland and C. L. Willis, Synthesis Of Fluorinated Amino Acids, Nat. Prod. Rep., 2000, 17, 621-631.
 
M. Cirilli, G. Scapin, A. Sutherland, J. C. Vederas and J. S. Blanchard, The Three-Dimensional Structure Of The Ternary Complex Of Corneybacterium glutamicum Diaminopimelate Dehydrogenase-NADPH-L-2-Amino-6-Methylene-Pimelate, Protein Science, 2000, 9, 2034-2037.
 
J. R. Harding, R. A. Hughes, N. M. Kelly, A. Sutherland and C. L. Willis, Syntheses of Isotopically Labelled L-α-Amino Acids With An Asymmetric Centre at C-3, J. Chem. Soc., Perkin Trans. 1, 2000, 3406-3416.
 
C. W. Koo, A. Sutherland, J. C. Vederas and J. S. Blanchard, Identification of Active Site Cysteine Residues That Function As General Bases: Diaminopimelate Epimerase, J. Am. Chem. Soc., 2000, 122, 6122-6123.
 
R. J. Cox, A. Sutherland and J. C. Vederas, Bacterial Diaminopimelate Metabolism As A Target For Antibiotic Design, Bioorg. Med. Chem., 2000, 8, 843-871.
 
G. Bhalay, S. Clough, L. McLaren, A. Sutherland and C. L. Willis, Synthesis and Enzyme-Catalysed Reductions Of 2-Oxo Acids With Oxygen Containing Side-Chains, J. Chem. Soc., Perkin Trans. 1, 2000, 901-910.
 
M. D. Fletcher, J. R. Harding, R. A. Hughes, N. M. Kelly, H. Schmalz, A. Sutherland and C. L. Willis, Three Approaches To The Synthesis Of L-Leucine Selectively Labelled With Carbon-13 Or Deuterium In Either Diastereotopic Methyl Group, J. Chem. Soc., Perkin Trans. 1, 2000, 43-52.
 

1999

A. Sutherland and J. C. Vederas, The First Isolation Of An Alkoxy-N,N-Dialkylaminodifluorosulfane From The Reaction Of An Alcohol And DAST: An Efficient Synthesis Of (2S,3R,6S)-3-Fluoro-2,6-Diaminopimelic Acid, Chem. Commun., 1999, 1739-1740.
 
A. Sutherland and C. L. Willis, Synthesis Of Probes For The Active Site Of Leucine Dehydrogenase, Bioorg. Med. Chem. Lett., 1999, 9, 1941-1944.
 
A. Sutherland, J. F. Caplan and J. C. Vederas, Unsaturated α-Aminopimelic Acids As Potent Inhibitors Of meso-Diaminopimelic Acid (DAP) D-Dehydrogenase, Chem. Commun., 1999, 555-556.
 
M. Frank, E. Kingston, J. C. Jeffery, M. O. Moss, M. Murray, T. J. Simpson and A. Sutherland, Walleminol and Walleminone, Novel Caryophyllenes From The Toxigenic Fungus Wallemia sebi, Tetrahedron Lett., 1999, 40, 133-136.
 

1996-1998

A. Sutherland and C. L. Willis, Chemoenzymatic Synthesis Of 4-Amino-2-Hydroxy Acids: A Comparison Of Mutant And Wild-Type Oxidoreductases, J. Org. Chem., 1998, 63, 7764-7769.
 
M. D. Fletcher, N. M. Kelly, A. Sutherland and C. L. Willis, “EnantioselectiveSynthesis Of L-α-Amino Acids Incorporating Stable Isotopic Labels,” In “Synthesis And Applications Of Isotopically Labelled Compounds 1997,” eds. J. R. Heys and D. G. Melillo, Wiley, 1998, 161-164.
 
A. Sutherland and C. L. Willis, Synthesis Of α-Amino-β-Hydroxy Acids, [¹⁵N]-L-alloThreonine And [¹⁵N]-L-Threonine, Tetrahedron Lett., 1997, 38, 1837-1840.
 
N. M. Kelly, A. Sutherland and C. L. Willis, Syntheses Of Amino Acids Incorporating Stable Isotopes, Nat. Prod. Rep., 1997, 14, 205-220.
 
A. Sutherland and C. L. Willis, Synthesis Of [6-¹³C]-L-Lysine, J. Labelled Compds. Radiopharm., 1996, 38, 95-102.