The novel areno-annelated estra-1,3,5(10),6,8,11,14,16-octaenes are synthes
ized in a simple, four-step protocol. The preparation includes a new areno-
annelation of an alpha -bromo-delta -nitrodiene 3 incorporating a domino He
ck-cyclisation-aromatisation sequence with the nitro functionality acting a
s 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.