Efficient preparations of anthracyclinones (1. and 21, the aglycones of the clinically important anthracycline antibiotics, daunorubicinl and adriamycin* require a regiospecific synthesis of the tetracyclic skeleton with proper orientation of rings A and D substituents. One attractive route to 1 would entail the direct regiospecific cyclization of the anthraguinone intermediate, 3 2. However, numerous attempts to catalyze the cyclization of 2 using conventional strong acidic (HF, cont. H2S04, PPA, BF3.Et20) or basic (NaH) reagents were unsuccessful. By altering the electronic configuration of the anthraguinone ring system, we were able to transform dihydroanthraquinone derivatives into anthracyclinones via intramolecular Claisen and aldol type condensations, which is the subject of this letter. LRl=H 3 2 Rl = OH R = H or CH 3 Condensation of phthalic anhydride with methylhydroguinone (A1C13/NaC14, 190' C) afforded 2-methyl-1,4-dihydroxyanthraguinone (A), m.p. 178-179' in 80% yield. Methylation of 4 ( (CH3)2S04/K2C03) afforded 2 (855, m.p. 132.5-133.5' C), which was brominated (NBS/CC14) to give 2 (SOS, m.p. 184-186'1, Nmr' (CDC13) 8 8.15 (m, 2H), 7.70 (m, 2H), 7.38 (s, lH), 4.61 (8, 2H), 4.01 (s, 3H), 4.00 (8, 3H). Alkylation (N&i/DMF, O" C) of 2 with 3-acetyl-4-oxo-valeric acid