Skip to content

Diacetone Mannose Synthesis Essay

The dimannosylatedinositol pseudotrisaccharide phospholipid of the lipoarabinomannan (LAM) component of the mycobacterial cell wall has attracted interest as a therapeutic target because of its uniqueness to mycobacteria, its assembly at an early stage in LAM biosynthesis and the immunological activity of oligosaccharides containing this subunit. Accordingly, analogues of this pseudotrisaccharide, α-D-mannose-(1 → 2)-α-D-mannose-(1 → 6)-D-myo-inositol are of interest as mechanistic probes and drug leads. C-glycosides are of special interest because of their hydrolytic stability and conformational differences compared to O-glycosides. Herein, as a prelude to C-glycoside analogues of this pseudotrisaccharide, we describe the synthesis of the C-glycoside of α-D-mannose-(1 → 6)-D-myo-inositol. The synthetic strategy centers on the elaboration of a C1-linked glycal-inositol, the glycone segment of which is assembled via an oxocarbenium ion cyclization on a thioacetal-enol ether precursor that originates from “glycone” and “aglycone” components.

Citation data is made available by participants in Crossref's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search inSciFinder.

  • Olefin Ring-Closing Metathesis



  • Applications in the Synthesis of Natural and Biologically Active Molecules



  • Ring-Closing Metathesis

    Bianca J.van LieropJustin A. M.LummissDeryn E.Fogg


  • 5.29 Ring-Closing Metathesis



  • Simple and efficient synthesis of highly functionalized cyclohexanes; formal total synthesis of ovalicin and fumagillin

    ShunyaTakahashiYayoiHongoYue QiYeHiroyukiKoshino

    Tetrahedron: Asymmetry201122 (6), 703-707

  • Syntheses of Fumagillin and Ovalicin


    Chemistry - A European Journal201016 (13), 3884-3901

  • NicolasBlanchardJacquesEustache


  • Total syntheses of (±)-ovalicin, C4(S∗)-isomer, and its C5-analogs and anti-trypanosomal activities

    Duy H.HuaHuipingZhaoSrinivas K.BattinaKaiyanLouAna L.JimenezJohnDesperElisabeth M.PerchelletJean-Pierre H.PerchelletPeter K.Chiang

    Bioorganic & Medicinal Chemistry200816 (9), 5232-5246

  • Transition metals in organic synthesis: Highlights for the year 2005

    Björn C.G.Söderberg

    Coordination Chemistry Reviews2008252 (1-2), 57-133

  • The chemistry of the carbon–transition metal double and triple bond: Annual survey covering the year 2005☆


    Coordination Chemistry Reviews2007251 (9-10), 1158-1258

  • Eine Diels-Alder-Route zu (−)-Ovalicin

    KonradTiefenbacherVladimir B.ArionJohannMulzer

    Angewandte Chemie2007119 (15), 2744-2747

  • A Diels–Alder Approach to (−)-Ovalicin

    KonradTiefenbacherVladimir B.ArionJohannMulzer

    Angewandte Chemie International Edition200746 (15), 2690-2693

  • Synthetic Strategies for Converting Carbohydrates into Carbocycles by the Use of Olefin Metathesis


    European Journal of Organic Chemistry20072007 (3), 399-415

  • Microwave-assisted ring-closing metathesis of diallylamines: a rapid synthesis of pyrrole and pyrroline derivatives


    Tetrahedron Letters200647 (23), 3893-3896