In continuation of our studies on aldol condensation of active methylene compounds, such as dihydrolevoglucosenone, with aldehydes1 containing no a-hydrogen atoms, we expanded the original protocol to include lipophilic aldehydes such as 1-formyl-adamantane. The starting 1-formyl adamantine was synthesized according to literature protocol from the corresponding alcohol. The condensation of the aldehyde with dihydrolevoglucosenone was performed in the presence of piperidine in ethanol. The crystalline product was isolated in 72 % yield and characterized by 1H and 13C NMR analysis. The product consists of highly hydrophobic adamantane unit and a highly hydrophilic moiety derived from the carbohydrate. Its biological profile is under investigation.

Synthesis of C-3 carbohydrate exo-cyclic enones via condensation of dihydrolevoglucosenone with adamantyl aldehyde

256th National Meeting (2018)

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