Construction of 1,6-anhydro-functionalized carbohydrate-fused spiro-chromanones via intramolecular
Nicole Jankowski1, Christopher Hager1, Holly Arcure2
1Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, United States.
Abstract:
The synthetic protocol for the first synthesis of carbohydrate-fused spiro-chromanones via intramolecular domino reaction between o-hydroxyacetophenones and dihydrolevoglucosenone (DHL) is described. The reactions proceed via the formation of an acetophenone (APh) enamine intermediate when performed in the presence of pyrrolidine in ethanol. The formation of a new carbon-carbon bond between nucleophilic carbon of the enamine of APh and C-2 of DHL is followed by cyclization, producing a new six-membered ring, as the result of an intramolecular domino process. Several substituted o-hydroxyacetophenones were reacted. The structure of products was determined using 1H and 13C NMR, GC-MS and X-ray crystallography. The yields are good to excellent (62-92 %), and the products are crystalline and easy to isolate. So far, the synthesized compounds were tested only for their antifungal properties. The results were disappointing.
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