Levoglucosenone, a bicyclic enone that is easily produced from the pyrolysis of cellulose waste, has been previously functionalized in a number of ways. Its saturated derivative, dihydrolevoglucosenone, could be easily functionalized with aromatic substituents to form products that were previously thought to be impossible to synthesize. This fact additionally encouraged us to explore a direct base-catalyzed aldol condensation reactions of functionalized aromatic aldehydes with dihydrolevoglucosenone: a saturated ketone possessing an active methylene group. These reactions should produce, via C-C, bond formation, C-3 linked exo-cyclic analogs with a desired and predictable stereochemistry. The new aromatic exo-cyclic enones were synthesized by base (piperidine) catalyzed aldol condensation of aromatic aldehydes with dihydrolevoglucosenone. Characterization by 1H and 13C NMR spectroscopies indicates the formation of single products of high purity and very good 75-85% yields. These annulated anhydro-sugars are of interest due to their potential of biological activities as prototypes of new antibacterial agents.

Synthesis of novel exo-cyclic carbohydrate enones from dihydrolevoglucosenone via direct aldol condensation with aromatic aldehydes

254th National Meeting (2017)

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