0000000000444954

AUTHOR

Stefan Weck

showing 4 related works from this author

ChemInform Abstract: Sweet (Hetero)aromatics: Glycosylated Templated for the Construction of Saccharide Mimetics.

2011

Several general strategies for the construction of mono- and diglycosylated (hetero)aromatics as potential metabolically stable oligosaccharides are described.

Chemistryhealth occupationsOrganic chemistrymacromolecular substancesGeneral Medicineenvironment and public healthChemInform
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Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics

2011

Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

GlycosylationChemistryMetals and AlloysOligosaccharidesmacromolecular substancesGeneral ChemistryHydrocarbons AromaticCombinatorial chemistryCatalysisCycloadditionSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsTemplateCyclizationMaterials ChemistryCeramics and CompositesOrganic chemistrylipids (amino acids peptides and proteins)Chemical Communications
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ChemInform Abstract: Total Synthesis of (-)-Hymenosetin.

2016

Hymenosetin (I) and its N-methyl analogue are prepared in 11 and 8 steps, respectively, from citronellal employing an intramolecular Diels-Alder reaction as the key step.

chemistry.chemical_compoundchemistryIntramolecular forcefungiCitronellalHymenosetinOrganic chemistryTotal synthesisGeneral MedicinePyrrole derivativesChemInform
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Total Synthesis of (-)-Hymenosetin.

2015

The 3-decalinoyltetramic acid (−)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels–Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.

Circular dichroismBiological ProductsCycloaddition ReactionMolecular Structure010405 organic chemistryChemistryStereochemistryOrganic ChemistryAbsolute configurationDiastereomerTotal synthesisStereoisomerism010402 general chemistry01 natural sciencesPyrrolidinones0104 chemical scienceschemistry.chemical_compoundDecalinIntramolecular forceMoietyMoleculeThe Journal of organic chemistry
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