Four-directional synthesis of adamantane derivatives

Abstract

1-Adamantanemethanol, 1,3-adamantanedimethanol and 1,3,5,7-adamantanetetramethanol were converted into adamantanes functionalized with one or four (2R,1S)-2-formyl-1-cyclopropyl residues using Charette enantioselective cyclopropanation reactions and with one, two or four 4-ethoxy-(or 4-t-butoxy)-3-diazo-2,4dioxobutyl residues from aldehyde and diazo-acetate ester condensation reactions by 1-directional, 2directional or 4-directional syntheses. The synthesis of adamantane fused to cyclopentadiene is also reported.