92591-97-4Relevant articles and documents
Enantiospecific Synthesis of Shikimic Acid from D-Mannose: Formation of a Chiral Cyclohexene by Intramolecular Olefination of a Carbohydrate-derived Intermediate
Fleet, George W. J.,Shing, Tony K. M.,Warr, Steven M.
, p. 905 - 908 (2007/10/02)
An enantiospecific synthesis of (-)-shikimic acid from D-mannose in an overall yield of 39percent is described, in which the key step is an intramolecular Wadsworth-Emmons olefination reaction of a phosphonate.Nucleophilic displacement of triflate from benzyl 2,3-O-isopropylidene-5-O-trifluoromethylsulphonyl-α-D-lyxofuranoside by the sodium salt of t-butyl dimethoxyphosphorylacetate provides a rare example of substitution at the C-5 position of a furanose derivative by a carbanion.