Abstract
A library of exo-cyclic carbohydrate enones 2–13 were prepared via a base-catalyzed, highly stereoselective aldol condensation of dihydrolevoglucosenone 1 (cyrene) with various aromatic aldehydes. In the case of 4-chlorobenzaldehyde as a reactant, under conditions of the aldol condensation, exo-cyclic enone 9 and a secondary product 9A was isolated. When 2-pyridinecarboxaldehyde was used as a reactant, an unexpected spironolactone 19 was exclusively observed. 1H NMR, 13C NMR, MS analyses and single-crystal x-ray diffraction of the representative enone 9, the secondary product 9A, hemiketal 18, and spironolactone 19 unequivocally confirms the structural assignments. Mechanistic insights leading to the synthesized products are also proposed and discussed.
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