The alkylation and aroylation of tetracyclo[6.3.0(4,11).0(5,9)]undecan
e-2,7-dione (i.e., TCUD-2,7-dione) (1) are reported. The reaction of t
he lithium enolate of 1 in the presence of HMPA with alkyl halides (1.
5-2.0 equiv) gave bisalkylated products 3 only in moderate yields, acc
ompanied by a considerable amount of mono-aroyl products 4.