AbstractReductive cyclization of the 1‐hydroxy‐3‐(3‐oxoalkyl)‐9,10‐anthraquinones2, 9and10yields the angularly condensed cyclopenta[a]anthraquinones3, 21and22aunder neutral conditions (DMF/Na2S2O4). By contrast, the linear cyclopenta[b]anthraquinone23is isolated from10applying the usual alkaline Marschalk conditions (aqueous methanol, NaOH, Na2S2O4). The linearly condensed 5,12‐naphthacenequinones24–28of different degree of saturation are obtained in good combined yield from the corresponding 1‐hydroxy‐3‐(4‐oxoalkyl)‐9,10‐anthraquinones19and20under the condition