A synthesis of ammonium 3-deoxy-(d)-manno-2-octulosonate (ammonium kdo) from (d)-mannose via cobaloxime-mediated radical alkyl-alkenyl cross coupling

Bruce P. Branchaud, Mark S. Meier

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-(d)-manno-2-octulosonic acid (KDO) starting from (d)-mannose. The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxime mediated radical alkyl-alkenyl cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose. KMnO4 unmasking of the latent functionality in the α-ethoxyacrylonitrile moiety provides the α-hydroxyester moiety necessary for completion of the KDO synthesis.

Original languageEnglish (US)
Pages (from-to)3191-3194
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number26
DOIs
StatePublished - 1988

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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