In continuation of our studies on aldol condensation of active methylene compounds, such as dihydrolevoglucosenone (CyreneR), with aromatic and heterocyclic aldehydes1-2 containing no a-hydrogen atoms we decided to extend the condensation approach to aliphatic aldehydes containing a ring, such as those shown in the reaction scheme below. In order to examine the potential pharmacological and electronic effect of bioisosteric scaffolds at C-7 position we selected these aldehydes as depicted in scheme 1. The crystalline products were isolated in good yield (60-75%) and characterized by 1H and 13C NMR spectroscopy. A plausible reaction mechanism will be presented.

Reaction of selected aliphatic aldehydes with dihydrolevoglucosenone

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