Simon J F Macdonald

Publications (5)20.71 Total impact

• Article: Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside.

  Rebecca R Midtkandal, Philip Redpath, Samuel A J Trammell, Simon J F Macdonald, Charles Brenner, Marie E Migaud
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  ABSTRACT: 2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.
  Bioorganic & medicinal chemistry letters 06/2012; 22(16):5204-7. · 2.65 Impact Factor
• Article: A chemoenzymatic synthesis of 5a-carba-α-D-mannose-6-phosphate.

  Paula M Williams, Gary N Sheldrake, Simon J F Macdonald, Chris J Hamilton
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  ABSTRACT: An efficient chemical synthesis of 5a-carba-α-D-mannose and its enzymatic elaboration to 5a-carba-α-D-mannose-6-phosphate, using yeast hexokinase, is described.
  Carbohydrate research 07/2011; 346(10):1257-61. · 2.03 Impact Factor
• Article: A one pot three-step process for the synthesis of an array of arylated benzimidazoribosyl nucleosides.

  Jolanta Hałuszczak, Simon J F Macdonald, Marie E Migaud
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  ABSTRACT: A three-step one pot reaction/purification protocol was developed to facilitate rapid access to benzimidazole-based nucleosides, for which benzoylated benzimidazoribosyl nucleosides incorporating boronic esters were key reaction intermediates.
  Organic & Biomolecular Chemistry 03/2011; 9(8):2821-31. · 3.70 Impact Factor
• Article: A stereocontrolled method for the synthesis of D- and L-2-deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction.

  Rebecca R Midtkandal, Simon J F Macdonald, Marie E Migaud
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  ABSTRACT: A novel synthetic procedure has been developed that provides access to d/l-2-deoxy-C-nucleosides from 3,4-epoxytetrahydrofuran in seven steps and in moderate to good yields. The key chemical transformation was the Lewis acid catalysed intramolecular cyclisation reaction of an acetal for which the stereochemical outcome was dependent of the reagents' ratio.
  Chemical Communications 07/2010; 46(25):4538-40. · 6.17 Impact Factor
• Article: 5,5-Fused thiophene gamma-lactams as templates for serine protease inhibition.

  Marie E Migaud, Rupert C Wilmouth, Gary I Mills, Gareth J Wayne, Catherine Risley, Christopher Chambers, Simon J F Macdonald, Christopher J Schofield
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  ABSTRACT: Novel 5,5-fused thiophene lactams are potent inhibitors and acylating agents of HNE and PPE.
  Chemical Communications 07/2002; · 6.17 Impact Factor