Synthesis of the ansa-bridged benzofuranquinone (±)- tridentoquinone (±)-(1) is approached by construction of a C4 methyl ketone chain at the 3-position of 6-bromo-4,5,7-trimethoxy-2,2-dimethyl-2,3-dihydrobenzofuran (10) and alkylation at its 6-position leading after modification to a dimethyl C10 aldehydic chain. Closure of the ansa bridge by McMurry coupling of the aldehyde and ketone groups of the intermediate (33) with C8K/TiCl3 appears to occur, but in poor yield and with uncertain stereochemistry, and the synthesis has not been completed.