The Pagodane Route to Dodecahedranes: Total Synthesis and Chemistry of 4,9,14,19‐Tetrasubstituted [1.1.1.1]Pagodanes

The tetraketone 1 and the dimethoxydiketone 2, R = CH3, could prove to be important intermediates en route to dodecahedranes. They can be prepared in several steps in good yield from 7-tert-butoxynorbornadiene and tetrachlorocyclopentadienone dimethyl ketal. According to force field calculations the four sp2-hybridized C atoms in 1 should facilitate thermal cleavage of the central four-membered ring and a subsequent hydrogenation.