Synthesis of (3R)- and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids: The (3R)- and (3S)-fluoro analogues of (−)-shikimic acid
✍ Scribed by Roger Brettle; Richard Cross; Martyn Frederickson; Edwin Haslam; Fiona S. MacBeath; Gareth M. Davies
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 213 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0960-894X
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📜 SIMILAR VOLUMES
A stereoselective synthesis of (1 0 S,3R,4R)-4-acetoxy-3-(2 0 -fluoro-1 0 -trimethylsilyloxyethyl)-2-azetidinone as a new fluorine-containing intermediate towards b-lactams, is described. The synthetic key step relies upon the dynamic kinetic resolution (DKR) of ethyl 2-benzamidomethyl-4-fluoro-3-ox
The tide compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-pbenyl-4-[(S)-2,2-dimethyl-l,3dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)glyceraldehyde and cyclopentadiene.
4R\*,5R\*)-4-Acetylamino-5-diethylcarbamoylcyclohex-1-ene-1-carboxylic acid and (3R\*,4R\*)-4-acetylamino-3-diethylcarbamoylcyclohex-1-ene-1-carboxylic acid have been synthesised using a Diels-Alder tactic; both compounds are selective inhibitors of influenza A sialidase, the latter compound being p