The synthesis of highly functionalized [5.9.5]tricyclic systems closely related to jatrophatrione (1) and 9-epijatrophatrione (2) is described. The first set of experiments provides a route to the conjugated 7-methylene ketones 8 and 9, both of which resist migration of the exocyclic double bond to a position internal to the ring. Subsequent dihydroxylation studies define a convenient pathway from 3 to triketone 20, which has yet to exhibit a tendency to undergo appropriate dehydration at the tertiary carbinol center. The presence of a carbonyl group in ring C was shown not to be contributory to this low reactivity. Finally, a protocol involving formation of a bromo oxetane with subsequent introduction of a C8-C9 double bond and Grob fragmentation has shown promise for arrival at 1 and/or 2 by making available the diene 36.