0000000000444954
AUTHOR
Stefan Weck
ChemInform Abstract: Sweet (Hetero)aromatics: Glycosylated Templated for the Construction of Saccharide Mimetics.
Several general strategies for the construction of mono- and diglycosylated (hetero)aromatics as potential metabolically stable oligosaccharides are described.
Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics
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.
ChemInform Abstract: Total Synthesis of (-)-Hymenosetin.
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.
Total Synthesis of (-)-Hymenosetin.
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.