A total synthesis of (±)-taxodione (8) was achieved from 11 via ring-opening of the activated cyclopropyl ketone (Scheme 4). In this case, 11 was reacted with excess TMSCl and NaI in MeCN. Following an aqueous workup, this protocol provided iodide 12 in >95% yield. It was best not to purify this sensitive intermediate. Instead, alkyl iodide 12 was directly reduced with zinc powder to furnish 13 in 82% yield. Deprotection of the aryl ethers with BBr 3 then unveiled the corresponding catechol, which rapidly to oxidized 8 in 93% yield upon exposure to SiO 2 and oxygen. As such, this approach provided (±)-8 in 9 total steps and 41% overall yield from commercially available fragments 6a and b-cyclocitral.