The novel areno-annelated estra-1,3,5(10),6,8,11,14,16-octaenes are synthesized in a simple, four-step protocol. The preparation includes a new areno-annelation of an α-bromo-δ-nitrodiene 3 incorporating a domino Heck–cyclisation–aromatisation sequence with the nitro functionality acting as a leaving group. The framework of the resulting areno-annelated estra-1,3,5(10),16-tetraenes can be dehydrogenated easily with DDQ to give the title compounds.