A synthetic route to 3,7-disubstituted bicyclo[3.3.2]decanes

Abstract

2,7-Dioxohomoadamantan-1,3,6,8-tetracarboxylic acid has been prepared in good yield from Meerwein's ester, and found to undergo specific 3,6-bisdecarboxylation. Wolff–Kishner reduction of the product gives homoadamantane-1,8-dicarboxylic acid. Treatment of the corresponding bis-acid chloride with chlorocarbonyl-bis(triphenylphosphine)rhodium gives 1,8-dichlorohomoadamantane, which is readily converted into 7-methylenebicyclo[3.3.2]decan-3-one in a base-induced fragmentation reaction.