Enantiospecific synthesis of shikimic acid from D-mannose: Formation of a chiral cyclohexene by intramolecular olefination of a carbohydrate-derived intermediate

George W.J. Fleet, Tony K.M. Shing, Steven M. Warr

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Abstract

An enantiospecific synthesis of (-)-shikimic acid from D-mannose in an overall yield of 39% 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.

Original languageEnglish
Pages (from-to)905-908
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1984 Dec 1

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ASJC Scopus subject areas

  • Chemistry(all)

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