Publications by authors named "William T Stimpson"
The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde.
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- L-ido cyanohydrin (3) was synthesized from diacetone-D-glucose through a four-step process, achieving a 76% overall yield and a 90% yield via the cyanohydrin reaction of aldehyde (2).
- The synthesis can be scaled up to produce more than 1 mole of pure L-ido cyanohydrin (3).
- L-ido cyanohydrin (3) was converted into various derivatives, including 1,2-isopropylidine-protected L-ido nitrile (8) and iduronic amide (9), which were then used to create new heparin-related disaccharides through coupling reactions with gluc